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Self‐Folded Silyl Cavitands with In‐ and Outwardly Directed Allyl Groups
Author(s) -
Ohashi Kazuhiro,
Ito Kouhei,
Iwasawa Tetsuo
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301843
Subject(s) - chemistry , silylation , medicinal chemistry , organic chemistry , stereochemistry , catalysis
Abstract Cavitands endowed with in‐ and outwardly directed allylsilanes are described; epoxidation reactions of the allyl groups with meta ‐chloroperbenzoic acid are included. The synthesis of introverted and extroverted allylsilanes tethered to triquinoxaline‐spanned resorcinarenes was successfully achieved. Competitive epoxidation experiments between the two isomers disclosed that the introverted allyl was more reactive than the extroverted allyl, despite a clearly congested nuisance: the vase‐formed cavity would actively stabilize the reaction process.