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Some novel aspects of regioselectivity in 1,3 dipolar cycloadditions of 4h-1-benzopyran-4-thione

✍ Scribed by Arpan K. Baruah; Dipak Prajapati; Jagir Sandhu


Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
326 KB
Volume
44
Category
Article
ISSN
0040-4020

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✦ Synopsis


4H-1-Benzopyran-4-thione (1) reacted smoothly with nitrilimines (3a-e) to afford regioselective cycloadducts (4a-e) in good yields. In contrast, benzunitrile oxide (6) and aldonitrones (7a-d) reacted preferentially at the thione function. The unstable cycloadduct (8) or ( 9) ruptured to give as isolable products chromone (10) and phenyl isothiocyanate (11) and the thioamides (12a -d). This indirectly proves the site of attack of the dipole at the thione group.


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Investigation of 4-H-I-benzopyran-4-thione (BPT) in its triplet state was performed in a flash photolysis system. The kinetics of phosphorescence and transient triplet-triplet absorption decay of BPT were measured in deoxygenated solutions. The studies were made with both protic and aprotic solution