2-Chloro-1,4-benzodithiin 1,1,4,4-Tetraoxide – A Conjunctive Dienophile for the Preparation of Tetrasubstituted Polycyclic Olefins

✍ Scribed by Ottorino De Lucchi; Sergio Cossu

• Book ID: 101278294
• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 228 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199812)1998:12<2775::aid-ejoc2775>3.0.co;2-t

✦ Synopsis

1,4-benzodithiin 1,1,4,4-tetraoxide 11 is a reactive Upon reductive desulfonylation with sodium amalgam, the latter are transformed to tetrasubstituted polycyclic olefins dienophile that forms Diels-Alder adducts with a number of dienes. Adducts 17a-j undergo facile dehydrochlorination to 24-27. These olefins correspond to the cycloadducts that would theoretically have been formed by the cycloaddition give 2,3-substituted 1,4-benzodithiin tetraoxides 18a-j, which react further with another molecule of diene (the same of diatomic carbon with two molecules of diene, reacting in a Diels-Alder fashion. or a different one) affording the "double" adducts 19-23.