Small-Ring Compounds. XXXVI. 3-Methylenecyclobutyl Bromide and 1-Methylcyclobut-2-enyl Bromide

Autor:	Edgar F. Kiefer, John D. Roberts
Rok vydání:	1962
Předmět:	Allene General Chemistry Aqueous ethanol Ring (chemistry) Photochemistry Biochemistry Medicinal chemistry Catalysis Cycloaddition chemistry.chemical_compound Colloid and Surface Chemistry Reaction rate constant chemistry Bromide Solvolysis Acrylonitrile
Zdroj:	Journal of the American Chemical Society. 84:784-788
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja00864a021
Popis:	3-Methylenecyclobutyl bromide and 1-methylcyclobut-2-enyl bromide have been synthesized from the cycloaddition products of allene with acrylonitrile and vinyl benzoate. The rate constants for solvolysis of the two bromides in aqueous ethanol have been determined and correlated with the solvolysis rates of a series of analogous bromides. 1-Methylcyclobut-2-enyl bromide appears to exhibit some rate enhancement due to cross-ring s-type interaction of the electrons formally centered on the 3-position with the electron-deficient 1-position in the transition state.
Databáze:	OpenAIRE
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