Preparation of cyclobutanones

Details Preparation of cyclobutanones Preparation of cyclobutanones

1978-03-13

1980-08-05

Morgenstern, Norman

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

Organic compounds

Oxygen containing

260464, 260465D, 260465E, 260465F, 260465G, 260465H, 260465K, 260557R, 260557B, 260558R, 260559R, 560 37, 560 45, 560 48, 560 51, 560 53, 560 54, 560 55, 560 56, 560 59, 560 61, 560 62, 560 64, 560 65, 560118, 560119, 560123, C07C 4500, C07C 4502

Patent

active

042161720

ABSTRACT:
A process for the preparation of a cyclobutanone of the formula ##STR1## in which R.sup.1 to R.sup.6 each independently is a hydrogen, halogen, cyano, alkoxy, alkoxycarbonyl, carboxamido, dialkylphosphono, alkyl, cycloalkyl, aryl, aralkyl or alkenyl radical, or two of them together with the carbon atom to which each is linked form a ring,
comprising reacting an N,N-disubstituted carboxylic acid amide of the formula ##STR2## in which R.sup.7 and R.sup.8 each independently is an alkyl, cycloalkyl, alkenyl, aryl or aralkyl radical or together form a ring, with an inorganic acid halide, and then reacting the product with a tertiary amine, an olefin of the formula ##STR3## and a Lewis acid, and subsequently hydrolyzing the mass. Preferably isobutyric acid dimethylamide is employed as the carboxylic acid amide, phosgene is employed as the inorganic acid halide, triethylamine is employed as the tertiary amine and zinc chloride or titanium tetrachloride is employed as the Lewis acid. The products are known intermediates for insecticides.

REFERENCES:
patent: 3078306 (1963-02-01), von Schickl et al.
patent: 3129248 (1964-04-01), England
patent: 3408398 (1968-10-01), Martin
patent: 4028418 (1977-06-01), van den Brink et al.
Marchand-Brynaert et al., "J.A.C.S.", vol. 94:8 (1972), p. 2870.
Hoonaert et al., "Angew Chem.", 87, Jahn. 1975, Nr. 15, pp. 552-553.
Sidani et al., "Angew Chem.", 86, Jahn. 1974, Nr. 7, p. 272.
Echngsfeld et al., "Angew Chem.", 72, Jahn. 1960, Nr. 22, pp. 836-843.
Ghosey et al., "Angew Chem.", 81 Jahn. 1969, Nr. 12, p. 468.
Seebach, "Meth. du Org. Chem.", Houber Weyl, vol. 4/4, pp. 180-202 (1971).

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