Synlett 2017; 28(12): 1481-1485
DOI: 10.1055/s-0036-1588990
letter
© Georg Thieme Verlag Stuttgart · New York

Metal-Free Oxidative C=C Bond Cleavage of Electron-Deficient Enamines Promoted by tert-Butyl Hydroperoxide

Mehdi Adib*
a   School of Chemistry, College of Science, University of Tehran, P. O. Box 14155-6455, Tehran, Iran   Email: madib@khayam.ut.ac.ir
,
Rahim Pashazadeh
a   School of Chemistry, College of Science, University of Tehran, P. O. Box 14155-6455, Tehran, Iran   Email: madib@khayam.ut.ac.ir
,
Seyed Jamal Adin Gohari
b   Department of Chemistry, Imam Hossein University, Tehran, Iran
,
Fatemeh Shahsavari
c   National Petrochemical Company, Petrochemical Research and Technology Company, Tehran, Iran
› Author Affiliations
Further Information

Publication History

Received: 29 November 2016

Accepted after revision: 08 March 2017

Publication Date:
19 April 2017 (online)


Abstract

A novel tert-butyl hydroperoxide (TBHP)-promoted oxidative C=C double-bond cleavage of enamines is described. Heating a solution of an electron-deficient enamine in chlorobenzene at 80 °C in the presence of TBHP for two hours led to cleavage of the C=C bond. This study offers a new strategy to carry out C=O double-bond formation by the use of TBHP.

Supporting Information

 
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