Process for producing optically active 2-(2,2-dihalogenovinyl)-c

Details Process for producing optically active 2-(2,2-dihalogenovinyl)-c Process for producing optically active 2-(2,2-dihalogenovinyl)-c

1979-12-17

1981-11-10

Trousof, Natalie

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

260315, 2603472, 2603474, 260456R, 260456A, 260456P, 260465D, 26050119, 26050121, 536 6, 546 53, 546134, 546282, 549 66, 549 76, 549 77, 549 79, 560118, 560124, 562500, 562506, 568361, 568366, C07C 51487, C07C 5100, C07C 6760, C07C 6700

Patent

active

042999677

ABSTRACT:
There is described a new process for the preparation of optically active 2-(2',2'-dihalogenovinyl)-cyclopropane-1-carboxylic acids substituted in the 3 position, and derivatives thereof. A racemate of certain cyclobutanones is reacted with a sulfurous acid salt of an optically active base to obtain a mixture of diastereomeric 4-2-(2',2',2'-trihalogenoethyl)-cyclobutane-1-sulfonic acid salts; this mixture is then separated into the pure diastereomeric sulfonic acid salts. Either the pure diastereomeric sulfonic acid salts are converted directly to the desired optically active products, or the optically active cyclobutanones obtained from the pure diastereomeric sulfonic acids salts by decomposition is converted, in the presence of a base to the desired product. Optionally, the product, optically active 2-(2',2'-dihalogenovinyl)-cyclopropane-1-carboxylic acids can be converted to their 1',2'-dibromo derivatives. SU

REFERENCES:
patent: 4028418 (1977-06-01), Brink
patent: 4064174 (1977-12-01), Verbrugge
patent: 4179575 (1979-12-01), Martel
Eliel, "Stereochemistry of Carbon Compounds", pp. 49-52 (1962), QD 481, E5.
Derwent Abst. of Jap. Pat. No. 50-131, 195, and 51-143,647 and 51-36,441.
Elliott, "Synthetic Pyrethroids", Am. Chem. Soc., Washington, D.C., pp. 2-25 (1977).

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