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Improved syntheses of carbon-14 labelled 3-phenoxybenzyl [1R,cis]- and [lR,trans]-3–(2,2–dichlorovinyl)-2,2-dimethylcyclopropanecarboxylates

✍ Scribed by Iwao Nakatsuka; Fumiaki Shono; Akira Yoshitake

Publisher
John Wiley and Sons
Year
1977
Tongue
French
Weight
384 KB
Volume
13
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

3‐Phenoxybenzyl [1R,cis]‐3–2(2,2‐dichlorovinyl)‐2,2‐dimethyl‐cyclopropanecarboxylate (I) and its [1R,trans]‐isomer (II) were labelled with carbon‐14 at C‐2 position of the dichlorovinyl side chain for metabolic studies. The stereospecific syntheses were achieved according to the reaction scheme shown in Fig. 1. Wittig reaction of methyl [1R,cis]‐3‐formyl‐2,2‐dimethylcyclo‐propanecarboxylate with carbon‐^14^C tetrachloride followed by hydrolysis gave [1R,cis]‐3‐(2,2‐dichlorovinyl‐2–^14^C)‐2,2‐dimethylcyclopropanecarboxylic acid (VIa). Chlorination of the acid (VIa) and subsequent treatment of the resulting acid chloride with 3‐phenoxybenzyl alcohol afforded 3‐phenoxybenzyl [1R,cis]‐3–(2,2‐dichlorovinyl–2‐^14^C)‐2,2‐dimethylcyclopropane‐carboxylate (I) in the overall yield of 33%. Its [1R,trans]‐isomer (II) was also prepared in 35% yield by the similar procedures. The specific activities of I and II were 4.30 and 3.80 mCi/mmole respectively.

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