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Synlett 2001; 2001(11): 1767-1771
DOI: 10.1055/s-2001-18091
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Oxidation of Diphenyl Diselenide with 2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ). A New Method for the Electrophilic Phenylselenenylation of Alkenes under Mild Conditions

Marcello Tiecco* , Lorenzo Testaferri, Andrea Temperini, Luana Bagnoli, Francesca Marini, Claudio Santi
  • *Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, I-06100 Perugia, Italy; Fax + 39(075)5 85 51 16; E-mail: tiecco@unipg.it
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Publication Date:
29 October 2001 (online)

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The oxidation of diphenyl diselenide with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) represents a convenient mild method to produce a strongly electrophilic phenylselenium reagent. Clean phenylseleno methoxylations and hydroxylations of alkenes containing different types of functional groups can be effected by working in methanol or in acetonitrile and water, respectively. This new electrophilic reagent can also be employed to promote efficient cyclization reactions of alkenols to tetrahydrofurans or of alkenoic acids to lactones.

selenium - electrophilic additions - cyclization reactions