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Structure and Reactivity of an Isolable Seven‐Membered‐Ring trans ‐Alkene
Author(s) -
Hurlocker Brisa,
Hu Chunhua,
Woerpel K. A.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201410752
Subject(s) - alkene , tetrahydrofuran , electrophile , nucleophile , reactivity (psychology) , chemistry , diastereomer , ring (chemistry) , ring strain , stereochemistry , crystal structure , double bond , crystallography , polymer chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology , solvent
The isolation and characterization of a trans ‐oxasilacycloheptene is reported. Single‐crystal X‐ray crystallographic studies indicate a high level of strain and deviation from ideal geometry. Reactions with several electrophiles demonstrated the nucleophilicity of the CC double bond, affording oxasilacycloheptane and tetrahydrofuran products as single diastereomers.