New syntheses of alkenes and alkynes from amines
AG Godfrey, B Ganem
Index: Godfrey; Ganem Journal of the American Chemical Society, 1990 , vol. 112, # 9 p. 3717 - 3718
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Citation Number: 12
Abstract
N-Nitrosacarboxamides 1 undergo a highly-solvent-dependent thermal rearrangement at 80- 100" C via diazenes 2 to products derived either from diazoalkanes 3 (path a) or carbocationic intermediates 4 (path b, eq I).,-" Nitrosamides of primary n-alkylamines follow path a almost exclusively in nonpolar solvents where the initially formed diazoalkane and carboxylic acid rapidly recombine to ester 5 in high yield. s* 6
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