The reaction of p,p'-ditolyl sulfoxide with p-tolyllithium evidence for an aryne intermediate

✍ Scribed by Kenneth K. Andersen; Sandra A. Yeager; N.Bekir Peynircioglu

• Book ID: 104249079
• Publisher: Elsevier Science
• Year: 1970
• Tongue: French
• Weight: 216 KB
• Volume: 11
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)98262-0

✦ Synopsis

Several years ago, we reported on the reaction of diphenyl sulfoxide with phenyllithium which yielded diphenyl sulfide and diphenyl.2

Formation of triphenylsulfonium cation (eq 1, R=H) as an intermsdiate was proposed on the basis of its ready synthesis from diphenyl sulfoxide and phenylmagnesium bromide.3

The sulfonium cation was postulated to react with phenyllithium to give diphenyl sulfide and bensyne; the latter then went on to give diphenyl (eqs 2 and 3, R-H):

(RC~H~)~S-O + RC~H~LI ,-(RC6H4j3 S+ + LiO-