Mass Spectrometry in Structural and Stereochemical Problems. LXXV. 1 Occurrence of Alkyl Rearrangements in the Fragmentation of Some Formaldehyde Acetals2

P Brown, C Djerassi, G Schroll…

Index: Brown,P. et al. Journal of the American Chemical Society, 1965 , vol. 87, p. 4559 - 4569

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Citation Number: 11

Abstract

The mass spectra of a series of formaldehyde acetals of primary, secondary, and tertiary alcohols, and phenol, have been recorded. Deuterium labeling and high resolution mass spectrometry demonstrated the operation of three distinct alkyl rearrangement mechanisms, each involving elimination of formaldehyde. Plausible pathways for the formation of all other principal ions are presented.