Oxidation Adjacent to Oxygen of Alcohols by Activated DMSO Methods
1991; Elsevier BV; Linguagem: Inglês
10.1016/b978-0-08-052349-1.00191-8
Autores Tópico(s)Asymmetric Synthesis and Catalysis
ResumoThe nucleophilic nature of the sulfinyl oxygen of sulfoxides has been used to good effect in synthetic chemistry, most notably in the oxidation of primary and secondary alcohols to aldehydes and ketones using dimethyl sulfoxide (DMSO). The first report of the use of dimethyl sulfoxide in such an oxidation was due to Pfitzner and Moffatt,1 although Kornblum had previously demonstrated the use of dimethyl sulfoxide as an oxidant for the conversion of alkyl halides to aldehydes.2 There are now many examples of how advantageous the use of dimethyl sulfoxide can be, most notably in the oxidation of primary alcohols to aldehydes without overoxidation to carboxylic acids. Despite much activity in this area, resulting in a plethora of activated dimethyl sulfoxide reagents which behave as an oxidant, the method is still basically that originally described by Pfitzner and Moffatt. However, considerable practical improvements have been made by a number of groups, most notably that of Swern, who utilized oxalyl chloride as the activator, and the 'Swern oxidation' is now a well-established synthetic method.
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