First Synthesis of Bromo and
Chloro Derivatives of Baylis-Hillman Adducts Derived from
Nitroolefins: Application towards the Synthesis of a Dendrimer Core

Manickam Bakthadoss; Nagappan Sivakumar; Anthonisamy Devaraj

doi:10.1055/s-0030-1258409

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Synthesis 2011(4): 611-618
DOI: 10.1055/s-0030-1258409

PAPER

First Synthesis of Bromo and Chloro Derivatives of Baylis-Hillman Adducts Derived from Nitroolefins: Application towards the Synthesis of a Dendrimer Core

Manickam Bakthadoss*, Nagappan Sivakumar, Anthonisamy Devaraj
Dept. of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Fax: +91(44)22352494; e-Mail: bhakthadoss@yahoo.com;

Further Information

Publication History

Received 23 November 2010
Publication Date:
12 January 2011 (online)

Abstract
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Abstract

For the first time Baylis-Hillman adducts derived from nitroolefins have been conveniently transformed into a novel class of building blocks, 1-[(E)-3-bromo-2-nitroprop-1-enyl]arenes and 1-[(E)-3-chloro-2-nitroprop-1-enyl]arenes, in very good yields via an S_N2 reaction using simple reaction conditions. Further application of these compounds has been demonstrated for the synthesis of tris[(E)-2-nitro-3-arylallyl]amines as dendrimer cores.

Key words

Baylis-Hillman reaction - ammonium acetate - nitroalkenes - iron(III) chloride - hydrobromic acid

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