With catalytic amounts of chlorotrimethylsilane/dimethyl sulphoxide (CTMSO/DMSO) in acetonitrile benzylic alcohols have been found to give high yields of styrenes. By using stoicheiometric amounts of reagents, different reaction pathways are observed: an elimination-addition sequence occurs with secondary and tertiary alcohols affording vicinal dichloro derivatives, beta-chloro thioethers and allyl chlorides, whereas a nucleophilic substitution to the corresponding monochlorides occurs star-ting from primary and sterically hindered substrates.

THE REACTION OF BENZYLIC ALCOHOLS WITH CHLOROTRIMETHYLSILANE/DIMETHYL SULFOXIDE / Bellesia, Franco; Ghelfi, Franco; Pagnoni, Ugo Maria; Pinetti, Adriano. - In: GAZZETTA CHIMICA ITALIANA. - ISSN 0016-5603. - STAMPA. - 122:(1992), pp. 437-439.

THE REACTION OF BENZYLIC ALCOHOLS WITH CHLOROTRIMETHYLSILANE/DIMETHYL SULFOXIDE

BELLESIA, Franco;GHELFI, Franco;PAGNONI, Ugo Maria;PINETTI, Adriano
1992

Abstract

With catalytic amounts of chlorotrimethylsilane/dimethyl sulphoxide (CTMSO/DMSO) in acetonitrile benzylic alcohols have been found to give high yields of styrenes. By using stoicheiometric amounts of reagents, different reaction pathways are observed: an elimination-addition sequence occurs with secondary and tertiary alcohols affording vicinal dichloro derivatives, beta-chloro thioethers and allyl chlorides, whereas a nucleophilic substitution to the corresponding monochlorides occurs star-ting from primary and sterically hindered substrates.
1992
122
437
439
THE REACTION OF BENZYLIC ALCOHOLS WITH CHLOROTRIMETHYLSILANE/DIMETHYL SULFOXIDE / Bellesia, Franco; Ghelfi, Franco; Pagnoni, Ugo Maria; Pinetti, Adriano. - In: GAZZETTA CHIMICA ITALIANA. - ISSN 0016-5603. - STAMPA. - 122:(1992), pp. 437-439.
Bellesia, Franco; Ghelfi, Franco; Pagnoni, Ugo Maria; Pinetti, Adriano
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/11344
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