930-65-4Relevant articles and documents
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Slaugh,L.H.
, p. 1522 - 1526 (1965)
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MECHANISMS OF EPOXIDATIONS AND CHLORINATIONS OF HYDROCARBONS BY INORGANIC HYPOCHLORITE IN THE PRESENCE OF A PHASE-TRANSFER CATALYST.
Fonouni,Krishnan,Kuhn,Hamilton
, p. 7672 - 7676 (2007/10/02)
Inorganic hypochlorite in the presence of a quarternary ammonium salt (phase-transfer catalyst) not only epoxidizes several arenes to arene oxides in high yields but also converts toluene to alpha -chlorotoluene, anisole to ring chlorinated anisoles, and alkenes to a complex mixture of chlorinated and oxidized products, including the epoxide. More detailed studies with this system indicate the following: (1) the high-yield conversion of toluenes to benzyl chlorides proceeds with a deuterium isotope effect of 3. 6 and a rho ** plus value of minus 1. 7: (2) p-chloroanisole is the major product from anisole and is formed in a 22-fold greater quantity than o-chloroanisole; (3) the epoxidation of cis- and trans-alkenes is stereoselective but not completely stereospecific; (4) the chlorination of saturated hydrocarbons occurs with a selectivity that is experimentally identical with that of chlorine monoxide.