THE ACYLATION OF OLEFINS. I. THE ACETYLATION OF CYCLOHEXENE¹

Perepoxide intermediates in the conversion of some β-halohydroperoxides to allylic hydroperoxides by base

“…A solution of 6.2 g I-acetylcyclohexene (22) Reduction of 0.78 g of compound 3 with lithiuni aluniinum hydride produced 0.69 g (999,) of an oil which had ir and 'H nnir spectra identical t o those of the above material. methanol at 0°C was added 0 60 g (0.01 1 rnol) sodium hydroxide in I rnl water and 3 nil methanol, dropwise w~t h stirring.…”

The Use Of Trifluoroacetic Anhydride And Related Compounds In Organic Syntheses

“…This method of preparation must be compared with the conventional Friedel-Crafts synthesis, in which the olefin is treated with an acyl chloride and a Lewis acid, followed by the dehydrochlorination of the intermediate product with a tertiary amine (72). The use of trifluoroacetic anhydride dispenses with the preparation of the acid chloride and the overall yields are better (178). The reaction can be applied to the preparation of cyclic ketones by the intramolecular condensation of suitable olefinic acids (88).…”

Alkylation

“…Ulrich, Gentes, Lane, and Wallis (187) report on the reactions of organometallic compounds wdth alkylhalides namely sodium ethyl-and 2-chloro-octane. In the acetylation of olefins wdth acyl halides in the presence of Friedel-Crafts catalyst, chlorine and unsaturated ketone, or a mixture of both depending upon the conditions used, may be obtained according to Royals and Hendry (156). Alkylated thiophene compounds are prepared by vapor-phase reaction of thiophene and olefins, alcohols, ethers, or alkyl halides containing three or more carbon atoms in the presence of an acid-reacting catalyst, according to the patent issued to the Texaco Development Corporation (181).…”