Photochemistry of conjugated polyacetylenes: photoreaction of 1,4-diphenyl-1,3-butadiyne with dimethyl fumarate

✍ Scribed by Sang Jin Lee; Sang Chul Shim

• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 254 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)97023-0

✦ Synopsis

Irradiation of 1,4-diphenyl-1,bbutadiyne (DPB) with dimethyl fumarate (DMFu) in deaerated tetrahydrofuran yields a primary 1: 1 photoadduct I and further irradiation of the solution results in the formation of novel 1:2 photoadducts, II and Ill as the secondary photoadducts. The photochemistry of conjugated pofyacetylenes has received relatively rile attention compared to corresponding olefins. We had previously reported the photoreaction of 1,4-diphenyl-1,3butadiyne with some olefins such as 2,3dimethyl-2-butene(DMB) and dimethyl fumarate(DMFu).l(a) 0 0 -OX0 zo= =~+o:-' 96 CL x x O 2 a We obtained, however, 1:l cyclobutene and 1:2 cycfopropyl addiiion products from photoreactions of conjugated polyacetylenes with olefins,1 @He) and we have reinvestigated the photoreactions of DPB with the same olefins. Detailed study on the photoreaction of DPB with an electron rich olefin. DMB, has been reported'@) and our previous structural assignment of the products were proven to be incomplete and/or wrong. In this investigation, we report more detailed photocycloaddition reaction of DPB with an electron deficient olefin, Dh4Fu.