ISSN:
1434-193X
Keywords:
Heterocycles
;
Cycloadditions
;
Diatomic carbon
;
Sulfones
;
Alkenes
;
Polycycles
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
2-Chloro-1,4-benzodithiin 1,1,4,4-tetraoxide 11 is a reactive dienophile that forms Diels-Alder adducts with a number of dienes. Adducts 17a-j undergo facile dehydrochlorination to give 2,3-substituted 1,4-benzodithiin tetraoxides 18a-j, which react further with another molecule of diene (the same or a different one) affording the “double” adducts 19-23. Upon reductive desulfonylation with sodium amalgam, the latter are transformed to tetrasubstituted polycyclic olefins 24-27. These olefins correspond to the cycloadducts that would theoretically have been formed by the cycloaddition of diatomic carbon with two molecules of diene, reacting in a Diels-Alder fashion.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
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