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Free radical type addition of toluenesulfonyl cyanide to unsaturated hydrocarbons

✍ Scribed by Jim-Min Fang; Ming-Yi Chen

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
253 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

By catalysis of AIBN, tosyl cyanide adds in a regio-and stereoselective manner to unsaturated hydrocarbons, including alkenes, dienes and 1-hexyne. Accompanied intramolecular cyclization and ring cleavage were effected in reactions with norbornadiene, 1,5-cyclooctadiene and pinenes. Toluenesulfonyl cyanide (TsCN) has been successfully utilized in many synthetic aspects. Due to the strong induction of the sulfonyl group, TsCN functions as a CN transfer agent in reactions with C-, N-, 0-and Snucleophiles. 1 The reaction is thought to involve an addition-elimination process. TsCN a12so undergoes cycloadditions readily with 1,3-dienes and 1,3-

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