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Updated: May 18, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
(2E,4R,5R,6S)-2-(4,5,6-Trihy-droxy-cyclo-hex-2-en-1-yl-idene)acetonitrile
Abstract:
The crystal structure of the title compound, C(8)H(9)NO(3), is characterized by a complex three-dimensional hydrogen-bond network in which every mol-ecule is connected to six symmetry-related neighbours.
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Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.