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.

Synthesis of 3??Arylindole??2??carboxylates via Copper??Catalyzed Hydroarylation of o??Nitrophenyl??Substituted Alkynoates and Subsequent Cadogan Cyclization

[Yamamoto, Yoshihiko; Yamada, Satoshi; Nishiyama, Hisao Advanced Synthesis and Catalysis, 2011 , vol. 353, # 5 p. 701 - 706]

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

Abstract

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