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Anti‐Bredt Enol Ethers by Transannular Cyclization of Cycloalkynols
Author(s) -
Detert Heiner,
AnthonyMayer Christina,
Meier Herbert
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199207911
Subject(s) - enol , chemistry , enol ether , ether , stereochemistry , philosophy , organic chemistry , catalysis
The thermal cycloalkynol–oxabicycloalkene rearrangement provides a new entry to the hitherto poorly known group of anti‐Bredt enol ethers. As an example, above 180°C (!) enol ether 2 is formed quantitatively from 1 . This rearrangement is not limited to strained cycloalkynols.