US EPA

8460143 

Journal Article 

Condensation of Saturated Halides with Unsaturated Compounds. II. The Condensation of Alkyl Halides with Monohalolefins 

Schmerling, L 

1946 

Yes 

Journal of the American Chemical Society
ISSN: 0002-7863
EISSN: 1520-5126 

68 

8 

1650-1654 

English 

10.1021/ja01212a087 

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0000774078&doi=10.1021%2fja01212a087&partnerID=40&md5=ada005e06c1aa4938eb8ecfc1e950a9b
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1. The condensation of alkyl chlorides and bromides with monochloro- and bromoolefins in the presence of metal chlorides of the Friedel- Crafts type yields higher molecular weight dihaloalkanes. The reaction proceeds via the addition of the alkyl group and the halogen atom of the alkyl halide to the double bond of the haloolefin, the halogen adding to the carbon atom that holds the smaller number of hydrogen atoms. 2. The reaction of a number of alkyl halides (isopropyl, t-butyl, and t-amyl chlorides and t- butyl and t-amyl bromides) with some of the more readily available haloolefins (vinyl chloride, 2- chloropropene, allyl chloride and allyl bromide) is described. 3. The condensation products obtained from the t-alkyl halides are new compounds. They serve as intermediates for the synthesis of aldehydes, ketones, and olefins (and the corresponding paraffins) containing quaternary carbon atoms. 4. Ethyl chloride could not be condensed with vinyl chloride. © 1946, American Chemical Society. All rights reserved.