Chemistry and Chemical Biology ETDs

Publication Date

10-14-1975

Abstract

The electron impact generated mass spectra of 13C- labeled trans-stilbene, bibenzyl, trans-stilbene oxide, 1,2-dibromo-1,2-dyphenylethane, and tolan were studied. Scrambling of the molecular ion prior to fragmentation was examined, and the scrambling pattern occurring was determined wherever possible. Synthesis of 1,α’-13C2-trans-stilbene was accomplished by strating with 1-13C- and 2-13C-acetic acid. 1,α’-13C2-bibenzyl, starting with 1,α’-13C2-trans-stilbene oxide, 1,α’-13C2-l,2-dibromo-l,2-diphen­ylechane, and 1,α’-13C2-tolan were all synthesized from the dilabeled stilbene. The mass spectral values for the phenyl ion, (pseudo)tropylium ion, (pseudo)phenylethyl ion, and M- methyl ion were com­pared with theoretical values calculated for four possible scrambling patterns: no scrambling, bridge carbon scrambling, tropylium scrambling, and total scrambling. All of the compounds had at least one fragment that exhibited evidence of molecular ion scrambling prior to its formation. Scrambling of the molecular ion of these types of compounds prior to fragmentation appears to be a fairly common occurrence. There is evidence that rearrangements other than the scrambling patterns postulated are occurring in some of the compounds studied.

Language

English

Document Type

Dissertation

Degree Name

Chemistry

Level of Degree

Doctoral

Department Name

Department of Chemistry and Chemical Biology

First Committee Member (Chair)

Ulrich Hollstein

Second Committee Member

William Fletcher Coleman

Third Committee Member

Eleftherios Paul Papadopoulos

Fourth Committee Member

Milton Kahn

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