Journal of Organometallic Chemistry p. 87 - 98 (1986)
Update date:2022-09-26
Topics:
Fobbe, Helmut
Neumann, Wilhelm P.
The photolytic reductive dimerization of a number of diaryl and aryl alkyl ketones by means of the distannane Me2(PhS)Sn-Sn(SPh)Me2 gives the corresponding 1,3,2-dioxastannolanes which are easily hydrolyzed yielding pinakols.Several diketones react in the same way with C-C coupling.Depending on the type of carbonyl compound, the different mechanism either exclude or compete with one another.One reaction proceeds via a ketyl radical ArRC.-OSn(SPh)Me2 and the bismetalated pinakol giving ultimately the five-membered ring and Me2Sn(SPh)2.However, with fluorinated acetones, a stannylenoid mechanism may be considered, and an organometallic 1,3-dipol RR'C--O-Sn+Me2 is proposed as a shortlived intermediate.
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