The Journal of Organic Chemistry

Synthesis and intramolecular cycloaddition reactions of some 3-substituted-6-azidohexa-2, 4-dienoate esters

RJ Sundberg, BC Pearce

Index: Sundberg, Richard J.; Pearce, Brad C. Journal of Organic Chemistry, 1982 , vol. 47, # 4 p. 725 - 730

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Citation Number: 19

Abstract

Results We chose, as the initial system for investigation, esters of 3-substituted-6-azidohexa- 2, 4-dienoic acids. It appeared these compounds could be made satisfactorily and with good flexibility as to the identity of the 3-substituent, by addition of a protected (3-hydroxy-cis-1- propeny1) copper to 3-substituted propynoate esters. Conversion of propargyl alcohol to the THP-protected (2)-vinyl iodide 2 proceeded via closely precedented4 iodination and ...