104108-29-4Relevant articles and documents
Photochemical 1,3-stannyl rearrangement of allylic stannanes
Takuwa, Akio,Kanaue, Takashi,Yamashita, Koichi,Nishigaichi, Yutaka
, p. 1309 - 1314 (2007/10/03)
The photochemical 1,3-stannyl rearrangement of allylic stannanes has been investigated. The photorearrangement of (E)-cinnamyl(triphenyl)stannane is not observed in benzene under anaerobic conditions, while the photoinduced 1,3-stannyl migration takes place in the same solvent under aerobic conditions, or in the presence of organic halides or a radical-trapping agent to give a photoequllibrium mixture of the cinnamylstannane and its branched regioisomer, 1-phenylprop-2-enyl(triphenyl)stannane, with the latter predominating. Cinnamyl(trialkyl)stannanes and their homologues also afford the corresponding branched allylstannanes under similar photochemical conditions. These 1,3-stannyl migrations proceed intramolecularly via cinnamyl π-π* excitation in competition with homolytic (cinnamyl)C-Sn bond fission. In contrast, the 1,3-stannyl migration of crotyl- and prenyl-(tributyl)-stannanes is not efficient, but their triphenyl or dibutylphenyl derivatives undergo the 1,3-rearrangement via excitation of the phenyl group(s) on the tin atom to give a regioisomeric mixture of the starting linear tin compounds and the branched ones with the former predominating.
Radical Reactions in Synthesis: Carbon-Carbon Bond Formation from 2-Substituted Allyl Trialkyl Stannanes
Baldwin, Jack E.,Adlington, Robert M.,Birch, David J.,Crawford, James A.,Sweeney, Joseph B.
, p. 1339 - 1340 (2007/10/02)
A competing 1,3-rearrangement of allyl stannanes has been demonstrated to occur under the normal thermal homolytic allyl transfer reaction conditions which limits the substitution patterns in these processes; two methacrylyl stannanes are described which allow the transfer of the methacrylyl moiety to alkyl bromides and iodides under mild conditions.
