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Syntheses of protoporphyrin-IX regioselectively carbon-13 labelled at the alpha-vinyl carbons

✍ Scribed by Kevin M. Smith; Eugene M. Fujinari

Publisher
John Wiley and Sons
Year
1986
Tongue
French
Weight
392 KB
Volume
23
Category
Article
ISSN
0022-2135

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✦ Synopsis

A method for transformation of readily available beta-vinyl 99% carbon-I3 enriched derivatives of protoporphyrin-IX dimethyl ester (3-5) into the less accessible alpha-vinyl labelled isomers (5-g) is described, -The procedure involves thallium(II1) promoted vinyl carbon rearrangement, and proceeds through 2,2-dimethoxyethyl (e.g. 101, formylmethyl (e.g. g), 2hydroxyethyl (e.g. and 2-chloroethyl 3 . g . 0) porphyrins; the rearranged vinyl groups are regenerated from 2-chloroethyl in the last step by treatment with base.

No evidence of vinyl carbon scrambling in the sequence is observed, and spectroscopic data of the products are given.

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