αpha;-Bromo Carbonyl Compounds as Promoters for the Synthesis of (2-Bromoethyl)benzene by the Anti-Markovnikov Addition of Hydrogen Bromide to Styrene

Ronny Neumann*, Fernando de la Vega, Adva Bar-On

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

The synthesis of (2-bromoethyl)benzene by the anti-Markovnikov addition of gaseous hydrogen bromide to styrene has been found to be promoted by αpha;-bromo carbonyl compounds such as 2-bromo-2-methylpropanal. These compounds were found to catalyze the “abnormal” addition in a variety of solvents such as ethyl acetate, heptane, toluene and dioxane. High concentrations of 2-bromo-2-methylpropanal and hydrogen bromide and low concentrations of styrene favor formation of (2-bromoethyl)benzene. Using the free-radical catalyzed cyclization of 6-bromo-l-hexene as a probe we have found that the 2-bromo-2-methylpropanal does not in itself initiate a free-radical chain reaction by thermal formation of radicals. Instead, radicals may react with 2-bromo-2-methylpropanal to form relatively stable 2-methylpropanal radicals. The presence of such radicals increases the effective length or inhibits termination of the free-radical chain reaction (propagation) and in the case of hydrobromination of styrene raises the yield of (2-bromoethyl)benzene.

Original languageEnglish
Pages (from-to)1315-1318
Number of pages4
JournalJournal of Organic Chemistry
Volume60
Issue number5
DOIs
StatePublished - 1 Mar 1995

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