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Diphenyl diselenide-assisted dithiolation of 1,3-dienes with diphenyl disulfide upon irradiation with near-UV light

โœ Scribed by Akiya Ogawa; Ryoichi Obayashi; Noboru Sonoda; Toshikazu Hirao

Book ID
104258692
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
145 KB
Volume
39
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

While the photoinduced reaction of 1,3-dienes with diphenyl disulfide provides a polymeric mixture, the same reaction in the presence of a catalytic amount of diphenyl diselenide provides the corresponding 1,4-dithiolation products (2) selectively in good yields. The higher carbon radical capturing ability of (PhSe) 2 and the reversibility of allylic selenides under photoirradiation contribute to the high efficiency of the conjugate addition of (PhS) z to 1,3-dienes under radical conditions.

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Selective sequential addition of dipheny
Selective sequential addition of diphenyl diselenide to ethyl propiolate and isocyanides upon irradiation with near-UV light
โœ Akiya Ogawa; Mikio Doi; Kaname Tsuchii; Toshikazu Hirao ๐Ÿ“‚ Article ๐Ÿ“… 2001 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 66 KB

Upon irradiation through Pyrex with a tungsten lamp (hw>300 nm), diphenyl diselenide adds to electron-deficient alkynes such as ethyl propiolate and isocyanides sequentially to provide the corresponding three-component coupling products in moderate to high yields selectively. The appropriate strengt