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O-sulfinylation with methanesulfonyl cyanide or p-toluenesulfonyl cyanide and DBU.

✍ Scribed by Derek H.R. Barton; Joseph Cs. Jaszberenyi; Emmanouil A. Theodorakis


Book ID
108380295
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
211 KB
Volume
32
Category
Article
ISSN
0040-4039

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Radical nitrile transfer with methanesul
✍ Derek H.R. Barton; Joseph Cs. Jaszberenyi; Emmanouil A. Theodorakis πŸ“‚ Article πŸ“… 1991 πŸ› Elsevier Science 🌐 French βš– 237 KB

Reaction of methanesulfonyl cyanide or p-toluenesulfonyl cyanide with carbon radicals generated from the acyl derivatives of N-hydroxy-2-thiopyridone gives the corresponding nitriles in high yield. A mechanistic scheme is suggested. There are many synthetic applications of carbon radicals generated

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Electrophilic Cyanations. Part 2. Synthesis of Heteroarenecarbonitriles by Electrophilic Cyanation: Reaction of Metalated Heteroarenes with p-Toluenesulfonyl Cyanide. -Carefull regioselective lithiation of hetarenes or even arenes (I) followed by addition of Tos-CN gives fair yields of (hetero)aren