Journal of Organic Chemistry p. 2051 - 2055 (1982)
Update date:2022-08-03
Topics:
Ojima, Iwao
Yatabe, Momoko
Fuchikami, Takamasa
The-Alder reactions of (trifluoromethyl)ethene (1) with 2-(trimethylsiloxy)buta-1,3-diene (2), 2-<(trimethylsilyl)methyl>-1,3-butadiene (4), and 1-methoxy-3-(trimethylsiloxy)buta-1,3-diene (6) were carried out to give the corresponding <4+2> cycloadducts in 17-38percent yields.It was found that the former two cycloadducts were a mixture of para (major) and meta (minor) isomers, while the latter was the para isomer exlusively.Similary, β-(trifluoromethyl)-4-(methoxycarbonyl)styrene (9) and β-(trifluoromethyl)-4-nitrostyrene (10) were allowed to react with 4 and 6, giving the corresponding <4+2> cycloadducts in 56-90percent yields.The regioselectivity of the reaction on using 6 as the diene turned out to be extremely high, leading to the formation of only one regioisomer.The substituent effect of the trifluoromethyl group in the Diels-Alder reaction in terms of regioselectivity is discussed.
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