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.
Pubblicazioni consigliate
I metadati presenti in IRIS UNIMORE sono rilasciati con licenza Creative Commons CC0 1.0 Universal, mentre i file delle pubblicazioni sono rilasciati con licenza Attribuzione 4.0 Internazionale (CC BY 4.0), salvo diversa indicazione.
In caso di violazione di copyright, contattare Supporto Iris
