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Beiträge zur Chemie des Bors, 220. Untersuchungen über Diborylmethane
Author(s) -
Ederer Bernd,
Metzler Nils,
Nöth Heinrich
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260906
Subject(s) - chemistry , isomerization , methylene , boron , medicinal chemistry , lithium (medication) , halogen , methane , carbon atom , yield (engineering) , derivatization , stereochemistry , organic chemistry , ring (chemistry) , catalysis , medicine , alkyl , materials science , high performance liquid chromatography , metallurgy , endocrinology
Contributions to the Chemistry of Boron 220 [1] . — Investigations on Diborylmethanes A convenient synthesis and spectroscopic properties of various organyl‐halogen‐substituted diborylmethanes (RXB) 2 CH 2 ( 2a — e , R = Me, Et, Pr, Ph, Mes) are described. Reaction of bis(dichloroboryl)methane ( 1 b ) with t BuLi in a 1:2 ratio leads to isomerization of the tert ‐butyl group, whereas bis(dimethoxyboryl)methane ( 1a ) reacts with 5 equivalents of t BuLi to yield tri‐ tert ‐butylborane and lithium di‐ tert ‐butylethyleneborate ( 9 ). Borate 9 is characterized NMR‐spectroscopically and by derivatization with Me 3 SiCl. Bis[alkinyl(dialkylamino)‐boryl]methanes 10a—c are obtained from the bis[chloro(dialkylamino)boryl]methanes 5a, b and LiCCPh or LiCCMe, respectively. 10c is characterized by an X‐ray crystal structure analysis which allows, for the first time, a direct comparison of an sp‐ and an sp 3 ‐carbon atom bound to the same boron atom. Finally, an almost linear relationship between dL 13 C of the methylene group and dL 11 B in diborylmethanes has been detected.