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Syntheses of water-soluble cationic porphyrins and chlorins

✍ Scribed by Ravindra K. Pandey; Fuu-Yau Shiau; Norman W. Smith; Thomas J. Dougherty; Kevin M. Smith

Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
952 KB
Volume
48
Category
Article
ISSN
0040-4020

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✦ Synopsis

Reactions of vinylchlorins and vinylporphyrins with N,N-dimethylmethyleneammonium iodide ("Eschenmoser's Reagent") gives Man&h adducts in which substitution (with CH2NMe2) has taken place on the terminal carbon of the vinyl group to yield a trans-3-(N,Ndimethylaminomethyl)prop-1 -enyl derivative. Under no circumstances was meso substitution observed. Use of zinc(II) vinylchlorins or zinc(II) vinylporphyrins afforded the corresponding zinc(I1) trans-vinyl adducts at a significantly faster rate than the metal-free substrates. Reaction of Eschenmoser's reagent with deuteroporphyrin-IX dimethyl ester (29) (which possesses two peripherally unsubstituted positions) produces the bis-(N,N-dimethylaminomethyl) product ( ). Treatment of the dimethylamino chlorins and porphyrins with methyl iodide, in all cases, gives an excellent yield of the corresponding quaternary ammonium iodides, and these compounds are highly water-soluble.

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