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Organic reactions of sulfur dioxide. 5. Reactions with cyclic dienes: a dual pathway for aromatization of the 1,3- and 1,4-cyclohexadienes

✍ Scribed by Divakar Masilamani; Milorad M. Rogić

Book ID: 104246082
Publisher: Elsevier Science
Year: 1978
Tongue: French
Weight: 216 KB
Volume: 19
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)95058-0

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✦ Synopsis

We proposed' that the facile regiospecific isomerization of trisubstituted olefins in liquid sulfur dioxide involves a reversible ene reaction of the olefin-sulfur dioxide adduct followed by the 1,3_rearrangement of the resulting allylic sulfinic acid intermediates, the retroene reaction, and elimination of sulfur dioxide.

We have also shown that the presence of water suppressed the above isomerization, and unexpectedly provided (with D20) a facile and direct method for regiospecific hydrogen/deuterium exchange of allylic hydrogens.2

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