Premium
1,1‐Ethylboration of alkyn‐1‐yl‐chloro(methyl)silanes: alkenes with chloro(methyl)silyl and diethylboryl groups in cis positions
Author(s) -
Wrackmeyer Bernd,
Shahid Khadija,
Ali Saqib
Publication year - 2005
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.882
Subject(s) - chemistry , silanes , silylation , triethylborane , intramolecular force , medicinal chemistry , boranes , stereochemistry , organic chemistry , catalysis , silane , boron
Abstract The 1,1‐ethylboration of alkyn‐1‐yl‐chloro(methyl)silanes, Me 2 Si(Cl)CCR ( 1 ) and Me(H)Si(Cl)CCR ( 2 ) [R = Bu ( 2a ), CH 2 NMe 2 ( 2b )] requires harsh reaction conditions (up to 20 days in boiling triethylborane), and leads to alkenes in which the boryl and silyl groups occupy cis (( E )‐isomers: 3a , 3b , 5a , 5b ) or trans positions (( Z )‐isomers in smaller quantities: 4b and 6b ). The alkenes are destabilized in the presence of SiH(Cl) and CH 2 NMe 2 units ( 5b , 6b ). NMR data indicate hyper‐coordinated silicon by intramolecular NSi coordination in 3b and 5b , by which, at the same time, weak SiClB bridges are favoured. Copyright © 2005 John Wiley & Sons, Ltd.