THERMAL FRAGMENTATION AND REARRANGEMENT OF β-KETOSULFIDE AND β-KETOSULFONE DERIVATIVES

Thermal fragmentation and rearrangement of neat phenacyl aryl sulfides I and II have been thoroughly investigated and found to involve cleavage of the C-S and C-C bonds followed by a series of H-abstraction, coupling, dimerization, rearrangement, and cyclization reactions. Also, in the presence of i...

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Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 1997-10, Vol.129 (1), p.135-145
Main Author: Gaber, Abd El-Aal M.
Format: Article
Language:English
Subjects:
Free radicals
Rearrangement
Thermal Fragmentation
β-Ketosulfides and sulfones
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Summary:Thermal fragmentation and rearrangement of neat phenacyl aryl sulfides I and II have been thoroughly investigated and found to involve cleavage of the C-S and C-C bonds followed by a series of H-abstraction, coupling, dimerization, rearrangement, and cyclization reactions. Also, in the presence of isoquinoline as a radical trap, I gave 1-phenyl- and 1-benzylisoquinoline in addition to the rearrangement products. Analogous results, beside SO 2 arylsulfonic acid and biaryl, were also obtained on heating phenacyl aryl sulfones III and IV in tetraline. A suitable mechanism has been suggested to account for the isolated products.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426509708031588