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Displacement of Activated Amino Groups. C,N- vs. N,S-Bond Cleavage in the Reaction of N-Alkyl-disulfonamides with Nucleophiles

✍ Scribed by Paul Müller; Minh Phuong Nguyen Thi

Publisher
John Wiley and Sons
Year
1979
Tongue
German
Weight
531 KB
Volume
62
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Sodiumthiophenoxide and sodiumphenylselenide react with N‐benzyl‐ and N‐hexyl‐di‐p‐toluenesulfonamides (1 and 2) via displacement at the C‐atom to afford the corresponding organosulfides and selenides in yields of 68–96%. In contrast, sodium cyanide converts disulfonamides to monosulfonamides by attack on the S‐atom. The different selectivities of phenylsulfide and selenide as compared to cyanide anions with respect to attack on the C‐ and S‐atoms are rationalized on the grounds of the HSAB (hard and soft acids and bases) principle of Pearson.

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