Preparation of 5H-dibenzo[a,d]cyclohepten-5-ones

Details Preparation of 5H-dibenzo[a,d]cyclohepten-5-ones Preparation of 5H-dibenzo[a,d]cyclohepten-5-ones

1987-12-18

1989-07-04

Reamer, James H.

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

Organic compounds

Oxygen containing

568322, 562840, C07C 4546

Patent

active

048453021

ABSTRACT:
5H-Dibenzo[a,d]cyclohepten-5-ones (I) ##STR1## (A and B being radicals for completing aromatic ring systems) are prepared by converting (Z)-2-(2-arylethenyl)arylcarboxylic acids (II) ##STR2## or E/Z-isomer mixtures thereof with a halogenating agent for carboxylic acids at from (-30.degree.) to +120.degree. C. to the corresponding carbonyl halides (III) ##STR3## where X is halogen, and cyclizing said carbonyl halides at from 0.degree. to 100.degree. C. in the presence of a Lewis acid.

REFERENCES:
Sethua et al. Friedel-Crafts & Related Reactions, vol. III, pp. 911-915 & 1058-1070 (1964).
Dibenztroponeacetic and -propionic Acids . . . Dunn et al., J. Med. Chem., 1977 vol. 20, No. 12, pp. 1557-1562.
Dibenzotropone-and Dibenzosuberonecarboxylic Acids . . . Dunn et al., J. Med. Chem. 1979, vol. 22, No. 11, pp. 1357-1363.
Chem. Ber. 84 (1951), pp. 671-679.
1-Methylene-2,3,6,7-Dibenzcycloheptatriene, COPE et al., J. Amer. Chem. Soc. 73 (Apr. 1951), pp. 1673-1678.

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