trans Deformation of a carbon–carbon triple bond in response to incipient nucleophilic attack: the X-ray crystal structure of ethyl 3-(2-nitrophenyl) propynoate at 150 K

CR Rice, JD Wallis

Index: Rice, Craig R.; Wallis, John D. Journal of the Chemical Society, Chemical Communications, 1993 , # 6 p. 572 - 574

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Citation Number: 7

Abstract

In the title compound 1 the electron-deficient alkyne bond shows a pronounced trans distortion in response to an adjacent electron rich nitro O atom, suggesting that the more favourable reaction coordinate for addition of nucleophiles to activated alkynes involves trans rather than cis addition.