205485-72-9

Basic information

• Product Name: (Z)-cinnamyl(triphenyl)stannane
• Synonyms: (Z)-cinnamyl(triphenyl)stannane
• CAS NO: 205485-72-9
• Molecular Weight: 467.198
• Mol File: 205485-72-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-cinnamyl(triphenyl)stannane(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-cinnamyl(triphenyl)stannane(205485-72-9)
• EPA Substance Registry System: (Z)-cinnamyl(triphenyl)stannane(205485-72-9)

Safety Data

• Hazardous Substances Data: 205485-72-9(Hazardous Substances Data)

Upstream product

• 29000-10-0 (E)-cinnamyl(triphenyl)stannane 

Relevant articles and documents

Photochemical 1,3-stannyl rearrangement of allylic stannanes

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.