Thesis-1978-Hollinshead.pdf (7.03 MB)
Download fileSome aspects of the chemistry of benzobicyclo systems
thesis
posted on 31.10.2018, 15:00 authored by John H. HollinsheadThe rearrangement reactions of 1-methoxybenzobicyclo-[2,2,2]-octatriene derivatives in strong acid have been studied. In particular 1-methoxytetrafluoro-, 1-methoxytetrachloro-, and 1-methoxybenzobarrelene
have been prepared labelled with 14C at C-4. Rearrangement of these
compounds, in strong acid, leads in each case, to three isomeric ketones.
The major product in each rearrangement was the corresponding benzobarrelenone,
formed, in each case, by two distinct pathways. The 14C
label in each benzobarrelenone was scrambled between C-4 and C-5
as a result of the two different mechanisms. A suitable degradation
procedure has been devised which allows the 14C activity in C-4 and
C-5 of each ketone to be determined, and hence an evaluation of the
percentage rearrangement which proceeds by the two mechanistic pathways
previously suggested. [Continues.]
Funding
Science Research Council.
History
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- Chemistry