Synthesis and structure of benzoboroxoles: Novel organoboron heterocycles

Viktor Zhdankin; P. J. Persichini; Lu Zhang; Shannon Fix; Paul Kiprof

doi:10.1016/S0040-4039(99)01303-9

Synthesis and structure of benzoboroxoles: Novel organoboron heterocycles

Viktor Zhdankin, P. J. Persichini, Lu Zhang, Shannon Fix, Paul Kiprof

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

68 Scopus citations

Abstract

Benzoboroxoles (5) can be prepared from the readily available o-bromobenzyl alcohols via dilithiation followed by reaction with triisopropylborate. X-Ray structural analysis of 1-hydroxy-3(1H)-1,2-benzoboroxole (5a) as well as the results of ab initio molecular orbital calculations indicate a planar structure of the boron center with a relatively short C-B bond. Preliminary results regarding the chemistry of benzoboroxoles are also reported.

Original language	English (US)
Pages (from-to)	6705-6708
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	37
DOIs	https://doi.org/10.1016/S0040-4039(99)01303-9
State	Published - Sep 10 1999

Bibliographical note

Funding Information:
This work was supportedb y the Camille and Henry Dreyfus Scholar/FellowP rogramfor Under-graduateIn stitutionsa nd a researchg rantfrom the National Science Foundation( NSF/CHE-9802823). Special thanks are made to Dr. Victor G. Young Jr. and the X-Ray CrystallographiLca boratoryo f the Universityo f Minnesotaf or X-ray structuraal nalysiso f compound5 a.

Keywords

Boron and compounds
Boron heterocycles
X-ray crystal structures

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title = "Synthesis and structure of benzoboroxoles: Novel organoboron heterocycles",

abstract = "Benzoboroxoles (5) can be prepared from the readily available o-bromobenzyl alcohols via dilithiation followed by reaction with triisopropylborate. X-Ray structural analysis of 1-hydroxy-3(1H)-1,2-benzoboroxole (5a) as well as the results of ab initio molecular orbital calculations indicate a planar structure of the boron center with a relatively short C-B bond. Preliminary results regarding the chemistry of benzoboroxoles are also reported.",

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T1 - Synthesis and structure of benzoboroxoles

T2 - Novel organoboron heterocycles

AU - Zhdankin, Viktor

AU - Persichini, P. J.

AU - Zhang, Lu

AU - Fix, Shannon

AU - Kiprof, Paul

N1 - Funding Information: This work was supportedb y the Camille and Henry Dreyfus Scholar/FellowP rogramfor Under-graduateIn stitutionsa nd a researchg rantfrom the National Science Foundation( NSF/CHE-9802823). Special thanks are made to Dr. Victor G. Young Jr. and the X-Ray CrystallographiLca boratoryo f the Universityo f Minnesotaf or X-ray structuraal nalysiso f compound5 a.

PY - 1999/9/10

Y1 - 1999/9/10

N2 - Benzoboroxoles (5) can be prepared from the readily available o-bromobenzyl alcohols via dilithiation followed by reaction with triisopropylborate. X-Ray structural analysis of 1-hydroxy-3(1H)-1,2-benzoboroxole (5a) as well as the results of ab initio molecular orbital calculations indicate a planar structure of the boron center with a relatively short C-B bond. Preliminary results regarding the chemistry of benzoboroxoles are also reported.

AB - Benzoboroxoles (5) can be prepared from the readily available o-bromobenzyl alcohols via dilithiation followed by reaction with triisopropylborate. X-Ray structural analysis of 1-hydroxy-3(1H)-1,2-benzoboroxole (5a) as well as the results of ab initio molecular orbital calculations indicate a planar structure of the boron center with a relatively short C-B bond. Preliminary results regarding the chemistry of benzoboroxoles are also reported.

KW - Boron and compounds

KW - Boron heterocycles

KW - X-ray crystal structures

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JO - Tetrahedron Letters

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ER -

Synthesis and structure of benzoboroxoles: Novel organoboron heterocycles

Abstract

Bibliographical note

Keywords

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