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Tandem energy transfer–electron transfer in the photosensitized alkylation of α,β-unsaturated ketones

✍ Scribed by Maurizio Fagnoni; Mariella Mella; Angelo Albini

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
62 KB
Volume
10
Category
Article
ISSN
0894-3230

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✦ Synopsis

␣,␤-Unsaturated ketones are not conveniently alkylated by radicals generated from tetraalkylstannanes via photoinduced electron transfer (PET), either by direct irradiation or when a singlet sensitizer (an aromatic nitrile, a pyrilium salt) is used. However, the procedure is successful with tetramethyl pyromellitate (TMPM) as the sensitizer. TMPM is promoted to the triplet state by energy transfer from the unsaturated ketones and then sensitizes the cleavage of alkylstannanes by electron transfer. The alkyl radicals thus formed finally add to the unsaturated ketones, giving the ␤-alkyl derivatives.

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✍ Tadashi Hasegawa; Masaaki Kajiyama; Yuko Yamazaki 📂 Article 📅 2000 🏛 John Wiley and Sons 🌐 English ⚖ 79 KB 👁 2 views

Alkyl aryl ketones undergo Type II photoreaction both on a silica-gel surface and in solution. The amount of acetophenone produced from valerophenone increases linearly with increase in the amount of valerophenone loaded at coverage below ca 60%. The effect of the alkyl chain length on the Type II p