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[2 + 2]‐Cycloreversions
Author(s) -
Schaumann Ernst,
Ketcham Roger
Publication year - 1982
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.198202253
Subject(s) - cycloaddition , regioselectivity , ring (chemistry) , olefin fiber , double bond , chemistry , group (periodic table) , kinetic energy , computational chemistry , organic chemistry , catalysis , physics , quantum mechanics
Abstract Four‐membered rings can be cleaved thermally, Photochemically, or catalytically into two π bonded fragments. Theoretical calculations, kinetic studies, and investigations of stereo‐ and regioselectivity have been undertaken to clarify the question of whether the reaction involves one or two steps and to permit predictions on its course. [2 + 2]‐Cycloreversions have been used to clarify the structure of four‐membered rings, to prepare highly reactive π electron‐systems and–in combination with a [2 + 2]‐cycloaddition–to protect double bonds. The combination of a cycloaddition and‐reversion can be used to convert a carbonyl group into an olefin. Starting with compounds containing annelated four‐membered rings, compounds with two functional groups or large ring systems can be prepared. [2 + 2]‐Cycloreversions have also been discussed in connection with storage of solar energy.