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{{Chembox
{{Chembox
| OtherNames = Boraneimine
| OtherNames = Boraneimine
| ImageFile = Iminoborane-dimensions-IR-1987-2D.png
| ImageCaption = Iminoborane (parent compound)
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| index_label = R,R'=H
| index_label = R,R'=H
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== Structure and bonding ==
== Structure and bonding ==
The parent iminoborane, HB=NH, is produced by the photolysis of H<sub>3</sub>BNH<sub>3</sub>.<ref>{{Cite journal|last1=Lory|first1=Earl R.|last2=Porter|first2=Richard F.|date=1973-03-01|title=Infrared studies of matrix isolated species in the hydrogen-boron-nitrogen system|journal=Journal of the American Chemical Society|volume=95|issue=6|pages=1766–1770|doi=10.1021/ja00787a012|issn=0002-7863}}</ref><ref>{{Cite journal|last1=Paetzold|first1=Peter|last2=Richter|first2=Anette|last3=Thijssen|first3=Theo|last4=Würtenberg|first4=Stefan|date=1979-12-01|title=Bildung, Struktur und Reaktivität von (Pentafluorphenyl)bor-tert-butylimid und seinem Cyclodimeren|journal=Chemische Berichte|language=en|volume=112|issue=12|pages=3811–3827|doi=10.1002/cber.19791121207|issn=1099-0682}}</ref><ref>{{Cite journal|last1=Paetzold|first1=Peter|last2=von Plotho|first2=Christoph|date=1982-08-01|title=Über weitere monomere Borimide und ihre Reaktionen|journal=Chemische Berichte|language=en|volume=115|issue=8|pages=2819–2825|doi=10.1002/cber.19821150813|issn=1099-0682}}</ref> Bonding in iminoboranes can be described by two [[Resonance (chemistry)|resonance structures]]:<ref>{{Cite journal|last1=Mó|first1=Otilia|last2=Yáñez|first2=Manuel|last3=Pendás|first3=Angel Martín|last4=Bene|first4=Janet E. Del|last5=Alkorta|first5=Ibon|last6=Elguero|first6=José|date=2007-07-23|title=Unusual substituent effects on the bonding of iminoboranes|url=http://xlink.rsc.org/?DOI=B702480K|journal=Phys. Chem. Chem. Phys.|language=en|volume=9|issue=30|pages=3970–3977|doi=10.1039/b702480k|pmid=17646885|bibcode=2007PCCP....9.3970M|issn=1463-9084|hdl=10261/72489}}</ref>
The parent iminoborane, HB=NH, is produced by the [[photodissociation|photolysis]] of H<sub>3</sub>BNH<sub>3</sub>.<ref>{{Cite journal|last1=Lory|first1=Earl R.|last2=Porter|first2=Richard F.|date=1973-03-01|title=Infrared studies of matrix isolated species in the hydrogen-boron-nitrogen system|journal=Journal of the American Chemical Society|volume=95|issue=6|pages=1766–1770|doi=10.1021/ja00787a012|issn=0002-7863}}</ref><ref>{{Cite journal|last1=Paetzold|first1=Peter|last2=Richter|first2=Anette|last3=Thijssen|first3=Theo|last4=Würtenberg|first4=Stefan|date=1979-12-01|title=Bildung, Struktur und Reaktivität von (Pentafluorphenyl)bor-tert-butylimid und seinem Cyclodimeren|journal=Chemische Berichte|language=en|volume=112|issue=12|pages=3811–3827|doi=10.1002/cber.19791121207|issn=1099-0682}}</ref><ref>{{Cite journal|last1=Paetzold|first1=Peter|last2=von Plotho|first2=Christoph|date=1982-08-01|title=Über weitere monomere Borimide und ihre Reaktionen|journal=Chemische Berichte|language=en|volume=115|issue=8|pages=2819–2825|doi=10.1002/cber.19821150813|issn=1099-0682}}</ref> Bonding in iminoboranes can be described by two [[Resonance (chemistry)|resonance structures]]:<ref>{{Cite journal|last1=Mó|first1=Otilia|last2=Yáñez|first2=Manuel|last3=Pendás|first3=Angel Martín|last4=Bene|first4=Janet E. Del|last5=Alkorta|first5=Ibon|last6=Elguero|first6=José|date=2007-07-23|title=Unusual substituent effects on the bonding of iminoboranes|url=http://xlink.rsc.org/?DOI=B702480K|journal=Phys. Chem. Chem. Phys.|language=en|volume=9|issue=30|pages=3970–3977|doi=10.1039/b702480k|pmid=17646885|bibcode=2007PCCP....9.3970M|issn=1463-9084|hdl=10261/72489}}</ref>
:<chem>R-\overset{\ominus}{B}{\equiv}\overset{\oplus}{N}-R <-> R-B=\ddot{N}-R</chem>
:HB<sup>−</sup><big><big><big>≡</big></big></big>N<sup>+</sup>H <big><big>↔</big></big> HB=NH


The stability is dramatically affected by bulky substituents. One isolable iminoborane is (tert-Bu)B=N(tert-Bu).<ref name=PPaetz>{{Cite journal|doi=10.1002/cber.19841170324|title=Darstellung, Reaktionen und Struktur vontert-Butyl(tert-butylimino)boran|year=1984|last1=Paetzold|first1=Peter|last2=Plotho|first2=Christoph Von|last3=Schmid|first3=Günter|last4=Boese|first4=Roland|last5=Schrader|first5=Bernhard|last6=Bougeard|first6=Daniel|last7=Pfeiffer|first7=Uwe|last8=Gleiter|first8=Rolf|last9=Schüfer|first9=Wolfgang|journal=Chemische Berichte|volume=117|issue=3|pages=1089–1102}}</ref>
The stability is dramatically affected by bulky substituents. One isolable iminoborane is {{chem2|(CH3)3C\sB−\tN+\sC(CH3)3}}.<ref name=PPaetz>{{Cite journal|doi=10.1002/cber.19841170324|title=Darstellung, Reaktionen und Struktur vontert-Butyl(tert-butylimino)boran|year=1984|last1=Paetzold|first1=Peter|last2=Plotho|first2=Christoph Von|last3=Schmid|first3=Günter|last4=Boese|first4=Roland|last5=Schrader|first5=Bernhard|last6=Bougeard|first6=Daniel|last7=Pfeiffer|first7=Uwe|last8=Gleiter|first8=Rolf|last9=Schüfer|first9=Wolfgang|journal=Chemische Berichte|volume=117|issue=3|pages=1089–1102}}</ref>


{| class="wikitable" style="text-align:center;"
{| class="wikitable" style="text-align:center;"
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|-
|-
! Molecule
! Molecule
| '''[[Ammonia borane]]'''<ref>{{ cite journal | first1 = L. R. | last1 = Thorne | first2 = R. D. | last2 = Suenram | first3 = F. J. | last3 = Lovas | title = Microwave spectrum, torsional barrier, and structure of BH<sub>3</sub>NH<sub>3</sub> | journal = [[The Journal of Chemical Physics|J. Chem. Phys.]] | volume = 78 | issue = 1 | year = 1983 | pages = 167-171 | doi = 10.1063/1.444528 }}</ref>
| '''[[Ammonia borane]]'''<ref>{{ cite journal | first1 = L. R. | last1 = Thorne | first2 = R. D. | last2 = Suenram | first3 = F. J. | last3 = Lovas | title = Microwave spectrum, torsional barrier, and structure of BH<sub>3</sub>NH<sub>3</sub> | journal = [[The Journal of Chemical Physics|J. Chem. Phys.]] | volume = 78 | issue = 1 | year = 1983 | pages = 167–171 | doi = 10.1063/1.444528 | bibcode = 1983JChPh..78..167T }}</ref>
| '''[[Aminoborane]]'''<ref>{{ cite journal | first1 = Masaaki | last1 = Sugie | first2 = Harutoshi | last2 = Takeo | first3 = Chi | last3 = Matsumura | title = Microwave spectrum and molecular structure of aminoborane, BH<sub>2</sub>NH<sub>2</sub> | journal = [[Journal of Molecular Spectroscopy|J. Mol. Spectrosc.]] | volume = 123 | issue = 2 | year = 1987 | pages = 286-292 | doi = 10.1016/0022-2852(87)90279-7 }}</ref>
| '''[[Aminoborane]]'''<ref>{{ cite journal | first1 = Masaaki | last1 = Sugie | first2 = Harutoshi | last2 = Takeo | first3 = Chi | last3 = Matsumura | title = Microwave spectrum and molecular structure of aminoborane, BH<sub>2</sub>NH<sub>2</sub> | journal = [[Journal of Molecular Spectroscopy|J. Mol. Spectrosc.]] | volume = 123 | issue = 2 | year = 1987 | pages = 286–292 | doi = 10.1016/0022-2852(87)90279-7 | bibcode = 1987JMoSp.123..286S }}</ref>
| '''[[Iminoborane]]'''<ref>{{ cite journal | first1 = Yoshiyuki | last1 = Kawashima | title = Detection of HBNH by infrared diode laser spectroscopy | journal = [[The Journal of Chemical Physics|J. Chem. Phys.]] | year = 1987 | volume = 87 | pages = 6331-6333 | doi = 10.1063/1.453462 }}</ref>
| '''Iminoborane'''<ref>{{ cite journal | first1 = Yoshiyuki | last1 = Kawashima | title = Detection of HBNH by infrared diode laser spectroscopy | journal = [[The Journal of Chemical Physics|J. Chem. Phys.]] | year = 1987 | volume = 87 | issue = 11 | pages = 6331–6333 | doi = 10.1063/1.453462 | bibcode = 1987JChPh..87.6331K }}</ref>
|-
|-
! Formula
! Formula
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| [[amine-borane]]
| [[amine-borane]]
| [[aminoborane]]
| [[aminoborane]]
| [[iminoborane]]
| iminoborane
|-
|-
! Analogous hydrocarbon
! Analogous hydrocarbon
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==Synthesis==
==Synthesis==


Elimination of fluoro- or chlorosilanes provides a well tested route. Bulky substituents such as [[tris(trimethylsilyl)silane|(Me<sub>3</sub>Si)<sub>3</sub>Si]] stabilize the iminoborane with respect to oligomerization:<ref>{{Cite journal|last1=Haase|first1=Martin|last2=Klingebiel|first2=Uwe|date=1985-04-01|title=Simple Synthesis of Stable Iminoboranes|journal=Angewandte Chemie International Edition in English|language=en|volume=24|issue=4|pages=324|doi=10.1002/anie.198503241|issn=1521-3773}}</ref>
Elimination of fluoro- or chlorosilanes provides a well-tested route. Bulky substituents such as [[tris(trimethylsilyl)silane|(Me<sub>3</sub>Si)<sub>3</sub>Si]] stabilize the iminoborane with respect to oligomerization:<ref>{{Cite journal|last1=Haase|first1=Martin|last2=Klingebiel|first2=Uwe|date=1985-04-01|title=Simple Synthesis of Stable Iminoboranes|journal=Angewandte Chemie International Edition in English|language=en|volume=24|issue=4|pages=324|doi=10.1002/anie.198503241|issn=1521-3773}}</ref>
:(Me<sub>3</sub>Si)<sub>3</sub>SiB(F)-N(SiMe<sub>3</sub>)<sub>2</sub> <big>→</big> (Me<sub>3</sub>Si)<sub>3</sub>Si-B=N-SiMe<sub>3</sub> + F-SiMe<sub>3</sub>
:(Me<sub>3</sub>Si)<sub>3</sub>SiB(F)-N(SiMe<sub>3</sub>)<sub>2</sub> <big>→</big> (Me<sub>3</sub>Si)<sub>3</sub>Si-B=N-SiMe<sub>3</sub> + F-SiMe<sub>3</sub>


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== Reactivity ==
== Reactivity ==
=== Oligomerization ===
=== Oligomerization ===
Iminoboranes tend to oligomerize, often forming cyclic derivatives. Preventing this reaction is the purpose of bulky substituents. Five types of oligomerization product are produced: cyclodimers (1,3,2,4-diazadiboretidines,<ref name=PPaetz/> '''Di'''<ref>{{Cite journal|last=Hess|first=H.|date=1969-11-15|title=Strukturbestimmungen an Bor–Stickstoff-Verbindungen. IV. Die Kristall- und Molekularstruktur von Hexakis(trimethylsilyl)-2,4-diamino-1,3,2,4-diazadiboretidin|journal=Acta Crystallographica Section B|language=de|volume=25|issue=11|pages=2342–2349|doi=10.1107/s056774086900567x|issn=0567-7408|url=http://journals.iucr.org/b/issues/1969/11/00/a06979/a06979.pdf}}</ref>), cyclotrimers ([[borazines]], '''Tr'''), bicyclotrimers ([[James Dewar|Dewar]] borazines, '''Tr’'''<ref>{{Cite journal|last1=Steuer|first1=Holger-A.|last2=Meller|first2=Anton|last3=Elter|first3=Gernot|title=B-t-butyl-borazine und -diazadiboretidine|journal=Journal of Organometallic Chemistry|language=en|volume=295|issue=1|pages=1–6|doi=10.1016/0022-328x(85)88065-7|year=1985}}</ref>), cyclotetramers (octahydro-1,3,5,7-tetraza-2,4,6,8-tetraborocines, '''Te'''<ref>{{Cite book|title=Turner H. S. and Warne R. J. 1962 Proc. Chem. Soc. 69}}</ref>), and polymers (polyiminoboranes, '''Po'''); which are shown below.<ref>{{Cite book|title=Advances in inorganic chemistry. Volume 31|date=1987|publisher=Academic Press|others=Emeléus, H. J. (Harry Julius), Sharpe, A. G.|isbn=978-0-12-023631-2|location=New York|oclc=277086713|url-access=registration|url=https://archive.org/details/trent_0116400835595_31}}</ref> Which product is dominant depends on the structures of reactants and the reaction conditions. Some of the products can be interconverted.<ref>{{Cite journal|last=Maier.G.|date=1978|title=Tetra-tert-butyltetrahedrane|journal=Angew. Chem. Int. Ed. Engl.|volume=17|issue=7|pages=520–521|doi=10.1002/anie.197805201}}</ref>
Iminoboranes tend to oligomerize, often forming cyclic derivatives. Preventing this reaction is the purpose of bulky substituents. Five types of oligomerization product are produced: cyclodimers ({{chem name|1,3-diaza-2,4-diboretidine}}s,<ref name=PPaetz/> '''Di'''<ref>{{Cite journal|last=Hess|first=H.|date=1969-11-15|title=Strukturbestimmungen an Bor–Stickstoff-Verbindungen. IV. Die Kristall- und Molekularstruktur von Hexakis(trimethylsilyl)-2,4-diamino-1,3,2,4-diazadiboretidin|journal=Acta Crystallographica Section B|language=de|volume=25|issue=11|pages=2342–2349|doi=10.1107/s056774086900567x|issn=0567-7408|url=http://journals.iucr.org/b/issues/1969/11/00/a06979/a06979.pdf}}</ref>), cyclotrimers ([[Borazine|borazines]], '''Tr'''), bicyclotrimers ([[Dewar benzene|Dewar]] borazines, '''{{prime|Tr}}'''<ref>{{Cite journal|last1=Steuer|first1=Holger-A.|last2=Meller|first2=Anton|last3=Elter|first3=Gernot|title=B-t-butyl-borazine und -diazadiboretidine|journal=Journal of Organometallic Chemistry|language=de|volume=295|issue=1|pages=1–6|doi=10.1016/0022-328x(85)88065-7|year=1985}}</ref>), cyclotetramers ({{chem name|octahydro-1,3,5,7-tetraza-2,4,6,8-tetraborocine}}s, '''Te'''<ref>{{Cite book|title=Turner H. S. and Warne R. J. 1962 Proc. Chem. Soc. 69}}</ref>), and polymers (polyiminoboranes, '''Po'''); which are shown below.<ref>{{Cite book|title=Advances in inorganic chemistry. Volume 31|date=1987|publisher=Academic Press|others=Emeléus, H. J. (Harry Julius), Sharpe, A. G.|isbn=978-0-12-023631-2|location=New York|oclc=277086713|url-access=registration|url=https://archive.org/details/trent_0116400835595_31}}</ref> Which product is dominant depends on the structures of reactants and the reaction conditions. Some of the products can be interconverted.<ref>{{Cite journal|last=Maier.G.|date=1978|title=Tetra-tert-butyltetrahedrane|journal=Angew. Chem. Int. Ed. Engl.|volume=17|issue=7|pages=520–521|doi=10.1002/anie.197805201}}</ref>


[[File:Figure product of iminboboranes oligomerization-1.png|453x453px|center|frameless]]
[[File:Figure product of iminboboranes oligomerization-1.png|453x453px|center|frameless]]
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[[Category:Boranes]]
[[Category:Boranes]]
[[Category:Amines]]
[[Category:Amines]]
[[Category:Boron-nitrogen compounds]]
[[Category:Boron–nitrogen compounds]]

Latest revision as of 10:01, 13 November 2024

Iminoborane

Iminoborane (parent compound)
Names
Other names
Boraneimine
Identifiers
3D model (JSmol)
  • R,R'=H: InChI=1S/BH2N/c1-2/h1-2H
    Key: LNLSXDSWJBUPHM-UHFFFAOYSA-N
  • R,R'=H: B=N
Properties
BH2N
Molar mass 26.83 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Structure of tBuN=B-tBu (tBu = tert-butyl). The B-N bond distance is 126 pm.[1]

Iminoboranes comprise a group of organoboron compounds with the formula RB=NR'. They are electronically related to acetylenes but are usually more reactive due to the polarity.[2][3]

Structure and bonding

[edit]

The parent iminoborane, HB=NH, is produced by the photolysis of H3BNH3.[4][5][6] Bonding in iminoboranes can be described by two resonance structures:[7]

The stability is dramatically affected by bulky substituents. One isolable iminoborane is (CH3)3C−B−≡N+−C(CH3)3.[1]

Comparison of bond lengths in simple boron-nitrogen hydrides
Molecule Ammonia borane[8] Aminoborane[9] Iminoborane[10]
Formula BNH6 BNH4 BNH2
Class amine-borane aminoborane iminoborane
Analogous hydrocarbon ethane ethylene acetylene
Analogous hydrocarbon class alkane alkene alkyne
Structure
Ball-and-stick model
Hybridisation of boron and nitrogen sp3 sp2 sp
B-N bond length 1.658 Å 1.391 Å 1.238 Å
Proportion of B-N single bond 100% 84% 75%
B-H bond length 1.216 Å 1.195 Å
N-H bond length 1.014 Å 1.004 Å
Structure determination method microwave spectroscopy microwave spectroscopy infrared spectroscopy

Synthesis

[edit]

Elimination of fluoro- or chlorosilanes provides a well-tested route. Bulky substituents such as (Me3Si)3Si stabilize the iminoborane with respect to oligomerization:[11]

(Me3Si)3SiB(F)-N(SiMe3)2 → (Me3Si)3Si-B=N-SiMe3 + F-SiMe3

Thermal decomposition of azidoboranes induces migration of R from boron to the nascent nitrene gives iminoboranes:[12]

R2B-N3 → RB=NR + N2

Reactivity

[edit]

Oligomerization

[edit]

Iminoboranes tend to oligomerize, often forming cyclic derivatives. Preventing this reaction is the purpose of bulky substituents. Five types of oligomerization product are produced: cyclodimers (1,3-diaza-2,4-diboretidines,[1] Di[13]), cyclotrimers (borazines, Tr), bicyclotrimers (Dewar borazines, Tr′[14]), cyclotetramers (octahydro-1,3,5,7-tetraza-2,4,6,8-tetraborocines, Te[15]), and polymers (polyiminoboranes, Po); which are shown below.[16] Which product is dominant depends on the structures of reactants and the reaction conditions. Some of the products can be interconverted.[17]

Addition reactions

[edit]

The addition of protic agents is fast and quantitive.[18] Boration reaction of iminoboranes is the addition of B-X single bond to B≡N, where -X can be -Cl (chloro-boration), -N3 (azido-boration), -SR (thio-boration), -NR2 (amino-boration) and R (alkyl-boration). One of these reactions are illustrated here.

Some electron-rich iminoboranes form adducts with Lewis acids.[19]

Cycloaddition

[edit]

The typical [2+3]-cycloaddition is the addition of B≡N and RN3 to give a BN4 ring.[1] One of the widely investigated [2+2]-cycloadditions is the reaction of aldehydes and ketones.

Coordination to transition metals

[edit]

Like alkynes, iminoboranes bind transition metals.

References

[edit]
  1. ^ a b c d Paetzold, Peter; Plotho, Christoph Von; Schmid, Günter; Boese, Roland; Schrader, Bernhard; Bougeard, Daniel; Pfeiffer, Uwe; Gleiter, Rolf; Schüfer, Wolfgang (1984). "Darstellung, Reaktionen und Struktur vontert-Butyl(tert-butylimino)boran". Chemische Berichte. 117 (3): 1089–1102. doi:10.1002/cber.19841170324.
  2. ^ Inorganic ring systems : 7th International symposium : Papers. Chivers, Tristram. Gordon and Breach Science Publishers. 1994. ISBN 978-2-88449-168-6. OCLC 81135356.{{cite book}}: CS1 maint: others (link)
  3. ^ Paetzold, Peter (1987). Iminoboranes. Advances in Inorganic Chemistry. Vol. 31. pp. 123–170. doi:10.1016/s0898-8838(08)60223-8. ISBN 978-0-12-023631-2.
  4. ^ Lory, Earl R.; Porter, Richard F. (1973-03-01). "Infrared studies of matrix isolated species in the hydrogen-boron-nitrogen system". Journal of the American Chemical Society. 95 (6): 1766–1770. doi:10.1021/ja00787a012. ISSN 0002-7863.
  5. ^ Paetzold, Peter; Richter, Anette; Thijssen, Theo; Würtenberg, Stefan (1979-12-01). "Bildung, Struktur und Reaktivität von (Pentafluorphenyl)bor-tert-butylimid und seinem Cyclodimeren". Chemische Berichte. 112 (12): 3811–3827. doi:10.1002/cber.19791121207. ISSN 1099-0682.
  6. ^ Paetzold, Peter; von Plotho, Christoph (1982-08-01). "Über weitere monomere Borimide und ihre Reaktionen". Chemische Berichte. 115 (8): 2819–2825. doi:10.1002/cber.19821150813. ISSN 1099-0682.
  7. ^ Mó, Otilia; Yáñez, Manuel; Pendás, Angel Martín; Bene, Janet E. Del; Alkorta, Ibon; Elguero, José (2007-07-23). "Unusual substituent effects on the bonding of iminoboranes". Phys. Chem. Chem. Phys. 9 (30): 3970–3977. Bibcode:2007PCCP....9.3970M. doi:10.1039/b702480k. hdl:10261/72489. ISSN 1463-9084. PMID 17646885.
  8. ^ Thorne, L. R.; Suenram, R. D.; Lovas, F. J. (1983). "Microwave spectrum, torsional barrier, and structure of BH3NH3". J. Chem. Phys. 78 (1): 167–171. Bibcode:1983JChPh..78..167T. doi:10.1063/1.444528.
  9. ^ Sugie, Masaaki; Takeo, Harutoshi; Matsumura, Chi (1987). "Microwave spectrum and molecular structure of aminoborane, BH2NH2". J. Mol. Spectrosc. 123 (2): 286–292. Bibcode:1987JMoSp.123..286S. doi:10.1016/0022-2852(87)90279-7.
  10. ^ Kawashima, Yoshiyuki (1987). "Detection of HBNH by infrared diode laser spectroscopy". J. Chem. Phys. 87 (11): 6331–6333. Bibcode:1987JChPh..87.6331K. doi:10.1063/1.453462.
  11. ^ Haase, Martin; Klingebiel, Uwe (1985-04-01). "Simple Synthesis of Stable Iminoboranes". Angewandte Chemie International Edition in English. 24 (4): 324. doi:10.1002/anie.198503241. ISSN 1521-3773.
  12. ^ Paetzold, Peter; Eleftheriadis, Eleftherios; Minkwitz, Rolf; Wölfel, Volker; Gleiter, Rolf; Bischof, Peter; Friedrich, Gert (1988-01-01). "Bildung, Struktur und Reaktionen von Methyl(methylimino)boran". Chemische Berichte. 121 (1): 61–66. doi:10.1002/cber.19881210110. ISSN 1099-0682.
  13. ^ Hess, H. (1969-11-15). "Strukturbestimmungen an Bor–Stickstoff-Verbindungen. IV. Die Kristall- und Molekularstruktur von Hexakis(trimethylsilyl)-2,4-diamino-1,3,2,4-diazadiboretidin" (PDF). Acta Crystallographica Section B (in German). 25 (11): 2342–2349. doi:10.1107/s056774086900567x. ISSN 0567-7408.
  14. ^ Steuer, Holger-A.; Meller, Anton; Elter, Gernot (1985). "B-t-butyl-borazine und -diazadiboretidine". Journal of Organometallic Chemistry (in German). 295 (1): 1–6. doi:10.1016/0022-328x(85)88065-7.
  15. ^ Turner H. S. and Warne R. J. 1962 Proc. Chem. Soc. 69.
  16. ^ Advances in inorganic chemistry. Volume 31. Emeléus, H. J. (Harry Julius), Sharpe, A. G. New York: Academic Press. 1987. ISBN 978-0-12-023631-2. OCLC 277086713.{{cite book}}: CS1 maint: others (link)
  17. ^ Maier.G. (1978). "Tetra-tert-butyltetrahedrane". Angew. Chem. Int. Ed. Engl. 17 (7): 520–521. doi:10.1002/anie.197805201.
  18. ^ Nöth, Heinrich; Weber, Siegfried (1985-05-01). "Beiträge zur Chemie des Bors, 154. Addition von Trimethylsily-Verbindungen und von anderen Elektrophilen an (tert-Butylimino) (tetramethylpiperidino)boran". Chemische Berichte. 118 (5): 2144–2146. doi:10.1002/cber.19851180536. ISSN 1099-0682.
  19. ^ Nöth, Heinrich; Weber, Siegfried (1985-06-01). "Beiträge zur Chemie des Bors, 158. Addukte von Aluminium- und Galliumhalogeniden an ein Aminoiminoboran". Chemische Berichte. 118 (6): 2554–2556. doi:10.1002/cber.19851180631. ISSN 1099-0682.
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