We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Displacement of Activated Amino Groups. C,N- vs. N,S-Bond Cleavage in the Reaction of N-Alkyl-disulfonamides with Nucleophiles.
- Authors
Müller, Paul; Thi, Minh Phuong Nguyen
- 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.
- Publication
Helvetica Chimica Acta, 1979, Vol 62, Issue 5, p1485
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19790620513