Free-radical reactions of allene the interaction of allene and thiyl radicals

✍ Scribed by H. J. van der Ploeg; J. Knotnerus; A. F. Bickel

• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 479 KB
• Volume: 81
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19620810908

✦ Synopsis

Abstract

The free‐radical addition of 1‐propanethiol, benzenethiol (thiophenol) and α‐toluenethiol (benzyl mercaptan) to allene in benzene solution has been investigated.

At high allene/thiol ratios the two sulfides resulting from the addition of one mole of RSH to allene (isopropenyl‐SR and allyl‐SR) are formed in yields of the same order of magnitude.

At low allene/thiol ratios the more reactive isopropenyl sulfide is not present among the products, since it is quantitatively converted into 1,2‐di‐SR‐propane. Thiol addition to the allyl sulfide to yield 1,3‐di‐SR‐propane is a much slower process.