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Diels–alder reactions of anthracenes with C-sulfonyldithioformates

✍ Scribed by Ibrahim El-Sayed; Omar M. Ali; Andreas Fischer; Alexander Senning

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
96 KB
Volume
14
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

C‐Sulfonyldithioformates (2) (R^1^ = ArSO~2~, R^2^ = ArS) readily add to anthracene and 9‐methylanthracene (1) in a Diels–Alder fashion with formation of 9,10‐dihydro‐10,9‐(epithiomethano)anthracenes (3) which in turn may suffer thermally induced elimination of arenesulfinic acid to yield the 9‐anthracenedithiocarboxylic esters (4). The reactions with the unsymmetrical diene 9‐methylanthracene take place in a highly stereoselective fashion. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:170–174, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10119

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