Process of preparing alkyl cis chrysanthemates

Details Process of preparing alkyl cis chrysanthemates Process of preparing alkyl cis chrysanthemates

1984-07-18

1985-11-05

Shippen, Michael L.

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

Organic compounds

Carboxylic acid esters

260455B, 548370, 549302, 549507, 562579, C07C 69747

Patent

active

045515450

ABSTRACT:
A process for the preparation of racemic or optically active isomers of alkyl esters of cis chrysanthemic of the formula ##STR1## wherein R is alkyl of 1 to 6 carbon atoms comprising reacting a racemic or optically active cis compound of the formula ##STR2## wherein R has the above definition with an aryl halothioformate of the formula ##STR3## wherein Hal is a halogen and Ar is aryl of 6 to 12 carbon atoms optionally substituted with at least one alkyl of 1 to 3 carbon atoms to obtain a compound of the formula ##STR4## of cis configuration and heating the latter optionally in an organic solvent to obtain the compound of formula I and novel intermediates.

REFERENCES:
patent: 3666738 (1972-05-01), Burke
patent: 3836568 (1974-09-01), Higo
patent: 4285882 (1981-08-01), Kramer
patent: 4289711 (1981-09-01), Lee
patent: 4346038 (1982-08-01), Kramer
Marek Majewski et al., "Synthesis of Pyrethroids Via Epoxyamide Cyclization", Tetrahedron Letter, vol. 23, No. 13, pp. 1343-1344, (1982).
H. Gerlach et al., "Synthesis of Olefins from Sterically Hindered Alcohols by Pyrolysis of Thiocarbonate O-Exters", J.C.S. Chem. Comm., (1972), pp. 1215-1216.

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