- PHOTOCHEMICAL CYCLOADDITION OF α,β-ACETYLENIC KETONES WITH SIMPLE OLEFINS
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Irradiation of 3-pentyn-2-one (1) in the presence of tetramethylethylene, isobutylene, and cis- and trans-2-butene leads to vinyldihydrofurans 3, 5, 6, 8, and 9 (Table 1) in a novel photochemical cycloaddition reaction.A related adduct 13 is formed between tetramethylethylene and 5,5-dimethyl-3-hexyn-2-one (2).A mechanism incorporating an initial biradical that closes to a carbene (eqn 3) is proposed to account for these reactions.
- Hussain, Saadat,Agosta, William C.
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p. 3301 - 3306
(2007/10/02)
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