Electron impact induced fragmentation of steroidal diketones with ‘abnormal’ stereochemistry

Donald George Jr Patterson, André Lavanchy, Carl Djerassi

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The mass spectral fragmentations of steroidal diketones with ‘unnatural’ sterechemistry at positions 8, 9 and 14 have been examined by the use of high resolution, metastable defocusing and isotopic labeling techniques. In addition, the elucidation of fragmentation pathways was greatly facilitated by the use of the INTSUM computer program. In contrast to 14α‐11‐ones, where the McLafferty rearrangement is of minor importance in directing the fragmentation, it is suggested that the ketones in the present study, by virtue of their ring C flexibility, readily undergo the McLafferty rearrangement. If correct, this would represent a further example of available ground state conformations controlling fragmentation after electron impact.

Original languageEnglish (US)
Pages (from-to)41-50
Number of pages10
JournalOrganic Mass Spectrometry
Volume15
Issue number1
DOIs
StatePublished - Jan 1 1980

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Stereochemistry
stereochemistry
Ketones
Labeling
Ground state
electron impact
Conformations
Computer program listings
fragmentation
Software
Electrons
isotopic labeling
defocusing
ketones
marking
flexibility
computer programs
ground state
rings
high resolution

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Instrumentation

Cite this

Patterson, Donald George Jr ; Lavanchy, André ; Djerassi, Carl. / Electron impact induced fragmentation of steroidal diketones with ‘abnormal’ stereochemistry. In: Organic Mass Spectrometry. 1980 ; Vol. 15, No. 1. pp. 41-50.
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Electron impact induced fragmentation of steroidal diketones with ‘abnormal’ stereochemistry. / Patterson, Donald George Jr; Lavanchy, André; Djerassi, Carl.

In: Organic Mass Spectrometry, Vol. 15, No. 1, 01.01.1980, p. 41-50.

Research output: Contribution to journalArticle

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