Olefins, Stereochemistry of Electrophilic Additions to Fahey

Fahey, R. C., The Stereochemistry of Electrophilic Additions to Olefins and Acetylenes, 3, 237. Farina, M., The Stereochemistry of Linear Macromolecules, 17, 1. 

Gyclohexene-l,3,3-d3, HBr in dry acetic acid, and 2,6-di-ferf-butyl-p-cresol to inhibit free-radical addition sealed in an ampoule and kept a few hrs. at 15° in a thermostat trans-addition product. Y 75-95% purity 91%. — This transaddition offsets the many examples of cts-addition to olefins and emphasizes that the stereochemistry of electrophilic additions is a sensitive function of olefin structure. R. G. Fahey and R. A. Smith, Am. Soc. 86, 5035 (1964). 

Electrophilic Additions to Olefins and Acetylenes, Stereochemistry of (Fahey) 3 237... 

---