Intramolecular cycloaddition reactions of dienyne ethers. Synthesis of bridgehead dienes and their thermal rearrangements

KJ Shea, LD Burke

Index: Shea, K. J.; Burke, L. D. Journal of Organic Chemistry, 1988 , vol. 53, # 2 p. 318 - 327

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Citation Number: 15

Abstract

The type 2 intramolecular Diels-Alder cycloaddition of dienyne ethers 13-16, 18, 19, and 22- 25 have been surveyed in both gas and solution phase. The dienyne ethers undergo cycloaddition to yield a novel class of bridgehead dienes of general structure 4. The stability and mode of thermal reactivity of the resulting bridgehead dienes varies as a function of the tether length. Bridgehead diene 37 has a half-life of 7 h at room temperature in dilute ...