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- W2000794110 abstract "Facial selectivity in the Diels-Alder reactions of 1,3-cyclopentadienes substituted at C-5 by a variety of simple alkyl groups has been assessed with a number of dienophiles. The results are consistent with an explanation based on steric hindrance. Syn addition is more favored with sterically less demanding dienophiles. Diene 6, which is substituted at C-5 with methoxymethyl, shows a remarkable preference for syn addition with less encumbered dienophiles. This may indicate a conformational difference in its syn transition state relative to the transition states for addition syn to methyl, ethyl, or n-butyl substituents (dienes 1, 4, and 5). Dienophiles are more reluctant to add syn to the larger C-5 group with 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene (2) and derivatives (3, and 7) and conformational effects become very important when C-5 bears two alkyl groups, as in dienes 3 and 7." @default.
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- W2000794110 date "1997-10-01" @default.
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- W2000794110 title "Diels−Alder Reactions of 5-Alkyl-1,3-cyclopentadienes" @default.
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- W2000794110 doi "https://doi.org/10.1021/jo9707949" @default.
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