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Preparation of trans-octaethylchlorin-D2(α,β),-D2(γ,δ), and -d4 as well as octaethylporphyrin-d2 using acid-catalyzed exchange reaction

✍ Scribed by Asaad Salehi; Harold N. Fonda; Anthony W. Oertling; Gerald T. Babcock; Chi K. Chang

Publisher
John Wiley and Sons
Year
1988
Tongue
French
Weight
191 KB
Volume
25
Category
Article
ISSN
0022-2135

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✦ Synopsis

Preparation of three forms of selectively deuterated transoctaethylchlorin (t-OEC) and octaethylporphyrin-d2 (OEP-d2) with high isotopic purity using acid catalyzed hydrogen-deuterium exchange reaction is described. Deuterated 1-OEC labeled at y,S-methine carbons was prepared directly by equilibrating 1-OEC in D2S04:D20 (6:l. v/v) at room temperature for 20 hours. 1-OEC labeled at all four methine carbons was prepared as above in 72 hours. And 1-OEC labeled at a$- positions was obtained by "back-exchange" of t-OEC-d4 under the protio condition, H2SOq:H20 (6:1, vh), in 18 hours. The DDQ dehydrogenation of either dideuterochlorin species resulted in the formation of OEP-d2. The isotopic purities of all deuterated compounds were over 98 percent except for t-OEC-d2(a,p) which was estimated to be -90 percent by proton NMR spectroscopy.

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