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Synlett 2008(17): 2557-2570  
DOI: 10.1055/s-2008-1078257
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Methods for Multiply Substituted Butadiene-Containing Building Blocks

Zhenfeng Xi*, Wen-Xiong Zhang*
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China
Fax: +86(10)62759728; e-Mail: zfxi@pku.edu.cn;
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Publication History

Received 14 April 2008
Publication Date:
22 August 2008 (online)

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Abstract

Conjugated organic systems have attracted much attention because new materials and functional structures can be expected from them. 2,4-Dienes mono- and disubstituted with electrophiles at the 1- and 1,6-positions, respectively, containing a butadienyl-conjugated skeleton and one or two terminal functional groups that can be manipulated, represent one of the most useful building units for the preparation of both cyclic and linear conjugated compounds. This account summarizes the synthetic methods available for multiply substituted butadiene-containing mono- or bis-electrophiles.

1 Introduction

2 Synthesis of Halobutadienes

2.1 1-Halobuta-1,3-dienes

2.2 1,4-Dihalobuta-1,3-dienes

3 Synthesis of Stereodefined Multisubstituted 1-Cyanobuta-1,3-dienes, 1,4-Dicyanobuta-1,3-dienes, and Related Compounds

4 Synthesis of 1-Lithiobuta-1,3-dienes and 1,4-Dilithiobuta-1,3-dienes

5 Synthesis of Buta-1,3-dienyl-Containing Amides, Alcohols, Imines, and Related Compounds

6 Synthesis of 2,4-Diene-1,6-dials, 2,4-Diene-1,6-diols, and Related Compounds

7 Conclusions and Perspectives

Key words

lithiobutadienes - conjugation - electrophiles - functionalized dienes - halobutadienes

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