tert-Butylacetylene revisited. Improved synthesis. Methyl migration during bromination

WL Collier, RS Macomber

Index: Collier,W.L.; Macomber,R.S. Journal of Organic Chemistry, 1973 , vol. 38, p. 1367 - 1369

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Citation Number: 39

Abstract

It has in fact been reported* that the bromination of 2, 3-dimethyl-1, 3-butadiene (5) at-15" gives two bromides, solid 7 (80%) stereochemistry unspecified, but probably trans considering steric effects) and a minor amount of a liquid dibromide (presumably 6), which could be interconverted at 100". We found that bromination of 5 at-10" yields two compounds with similar glc characteristics. They were initially present in comparable amounts, but ...