Mass spectrometry in structural and stereochemical problems. CCII. Interaction of remote functional groups in acyclic systems upon electron impact

C Djerassi, M Sheehan, RJ Spangler…

Index: Sheehan,M. et al. Journal of Organic Chemistry, 1971 , vol. 36, p. 1796 - 1804

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Abstract

In a series of 4-alkoxybutyrates and related substances, the scope and limitations of the unexpected p cleavage at the ether function have been investigated. Deuterium-labeling experiments and high resolution mass measurements indicated that no rearrangements or reciprocal hydrogen transfers were involved in this process. The intensity of the p-cleavage ion became unimportant as the alkoxy group increased in size. Major fragmentation ...