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Reactions of azides with carbonyl-stabilized sulfonium ylids.

✍ Scribed by E. Van Loock; G. Lábbé; G. Smets

Publisher
Elsevier Science
Year
1970
Tongue
French
Weight
189 KB
Volume
11
Category
Article
ISSN
0040-4039

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Carbonyl-stabilized sulfonium ylides readily react with elemental sulfur and selenium to afford 1,3-oxathiole and 1,3-oxaselenole derivatives, respectively, in good yields, thus providing a simple method for constructing these ring systems which uses easily accessible compounds as starting materials

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Nucleophiles such as hydride and hydroxide have previously been shown to readily react with pyrimidinium salts, and the products of these reactions can be rationalized on the basis of nucleophilic attack at the 2-position of the heterocycle (1,2,3).