Vicinal Dichlorination of Olefins Using NH4Cl and Oxone®

Peraka Swamy; Marri Mahender Reddy; Macharla Arun Kumar; Mameda Naresh; Nama Narender

doi:10.1055/s-0033-1340298

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(02): 251-257
DOI: 10.1055/s-0033-1340298

paper

Vicinal Dichlorination of Olefins Using NH₄Cl and Oxone^®

Peraka Swamy

Inorganic and Physical Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India Fax: +91(40)27160387 eMail: narendern33@yahoo.co.in

,

Marri Mahender Reddy

Inorganic and Physical Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India Fax: +91(40)27160387 eMail: narendern33@yahoo.co.in

,

Macharla Arun Kumar

Inorganic and Physical Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India Fax: +91(40)27160387 eMail: narendern33@yahoo.co.in

,

Mameda Naresh

Inorganic and Physical Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India Fax: +91(40)27160387 eMail: narendern33@yahoo.co.in

,

Nama Narender*

Inorganic and Physical Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India Fax: +91(40)27160387 eMail: narendern33@yahoo.co.in

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Abstract

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Abstract

A mild and efficient protocol for the preparation of 1,2-dichloroalkane derivatives from olefins using NH₄Cl and Oxone^® at room temperature is described. A variety of terminal, internal, and cyclic alkenes reacted smoothly to give the corresponding dichlorinated products in good to excellent yields. Moreover, 1,2-disubstituted symmetrical and unsymmetrical olefins dichlorinated with moderate to excellent diastereoselectivity. This method precludes the use of acidic additives and transition metals in the synthesis of vicinal dichlorides.

Key words

vicinal dichlorination - olefins - NH₄Cl - Oxone^® - diastereoselectivity

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Referenzen

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