Synthetic Photochemistry. LXIV. Mild Base-Induced retro-Benzilic-Acid Rearrangement of Isolated proto-Photocycloadducts of Methyl 2, 4-Dioxopentanoate to …

T Hatsui, JJ Wang, H Takeshita

Index: Hatsui; Wang; Takeshita Bulletin of the Chemical Society of Japan, 1994 , vol. 67, # 9 p. 2507 - 2513

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Citation Number: 13

Abstract

In the photoaddition reaction of terpinolene with methyl 2, 4-dioxopentanoate, the products derived from the tetrasubstituted C= C were four proto-[2+ 2] photocycloadducts, together with ene reaction products. When these proto-cycloadducts were treated with aqueous sodium carbonate, a facile retro-benzilic acid rearrangement to form substituted cyclopentenone derivatives occurred. The product from the other trisubstituted C= C was ...

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