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The Profound Effect of the Ring Size in the Electrocyclic Opening of Cyclobutene‐Fused Bicyclic Systems
Author(s) -
Ralph Michael J.,
Harrowven David C.,
Gaulier Steven,
Ng Sean,
BookerMilburn Kevin I.
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.201410115
Subject(s) - cyclobutene , ring (chemistry) , bicyclic molecule , propargyl , chromophore , chemistry , ring size , electrocyclic reaction , photochemistry , stereochemistry , organic chemistry , catalysis
Fused cyclobutenes, prepared by the photocycloaddition of propargyl alcohols to cyclic anhydride chromophores, undergo facile thermochemical ring opening to fused γ‐lactones. The size of the fused ring profoundly influences the temperature that is required to facilitate the ring opening (from 50 °C to 180 °C) and the nature of the product that is formed. Our studies provide new insights into the mechanistic course of these reactions and have been extended to facilitate the preparation of lactams fused to medium‐sized rings.