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Se ‐Phenyl Prop‐2‐eneselenoate: An Ethylene Equivalent for Diels–Alder Reactions
Author(s) -
Jung Michael E.,
Perez Felix,
Regan Collin F.,
Yi Sung Wook,
Perron Quentin
Publication year - 2013
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.201208294
Subject(s) - allylic rearrangement , chemistry , ether , ethylene , process (computing) , medicinal chemistry , acryloyl chloride , organic chemistry , computer science , acrylate , catalysis , programming language , polymer , monomer
Reactive : Se ‐phenyl prop‐2‐eneselenoate (phenyl selenoacrylate) 2 , readily prepared from acryloyl chloride, is a very reactive dienophile in Diels–Alder reactions, and more reactive than acrylates. Its cycloadducts 3 with many dienes 1 can be easily reduced to the hydrocarbons 4 under radical conditions. This process works even in cases where there is an adjacent group that can be easily eliminated, e.g., an allylic ether.