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The improved synthesis, Diels‐Alder reactions, and desulfuration of trithio‐1,8‐naphthalic anhydride

The improved synthesis, Diels‐Alder reactions, and desulfuration of trithio‐1,8‐naphthalic anhydride In the presence of a strong Lewis base, such as Et3N, trithio‐1,8‐naphthalic anhydride (3) is easily oxidized. Two improved syntheses of trithio‐1,8‐naphthalic anhydride (3) are described. Trithio‐1,8‐naphthalic anhydride (3) undergoes Diels‐Alder reactions with electron‐deficient alkenes to give novel fused heterocyclic compounds (6–11) that then can undergo a novel, gradual desulfuration dimerization with triethyl phosphite to afford 12 and its analogs 13 and 14. The structures of 6–14 are confirmed by microanalysis, IR, and NMR spectroscopy, and MS. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 141–146, 1999 http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

The improved synthesis, Diels‐Alder reactions, and desulfuration of trithio‐1,8‐naphthalic anhydride

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References (12)

Publisher
Wiley
Copyright
Copyright © 1999 John Wiley & Sons, Inc.
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/(SICI)1098-1071(1999)10:2<141::AID-HC7>3.0.CO;2-B
Publisher site
See Article on Publisher Site

Abstract

In the presence of a strong Lewis base, such as Et3N, trithio‐1,8‐naphthalic anhydride (3) is easily oxidized. Two improved syntheses of trithio‐1,8‐naphthalic anhydride (3) are described. Trithio‐1,8‐naphthalic anhydride (3) undergoes Diels‐Alder reactions with electron‐deficient alkenes to give novel fused heterocyclic compounds (6–11) that then can undergo a novel, gradual desulfuration dimerization with triethyl phosphite to afford 12 and its analogs 13 and 14. The structures of 6–14 are confirmed by microanalysis, IR, and NMR spectroscopy, and MS. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 141–146, 1999

Journal

Heteroatom ChemistryWiley

Published: Jan 1, 1999

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