The Journal of Organic Chemistry

Intramolecular Diels-Alder reaction of. alpha.,. beta.-unsaturated ester dienophiles with cyclopentadiene and the dependence on tether length

JR Stille, RH Grubbs

Index: Stille, John R.; Grubbs, Robert H. Journal of Organic Chemistry, 1989 , vol. 54, # 2 p. 434 - 444

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Citation Number: 31

Abstract

Cyclopentadiene compounds, tethered to an a,@ unsaturated ester functionality, have been prepared by the direct alkylation of the corresponding iodide or tosylate with cyclopentadienylmagnesium chloride. For example,~ O-CH, CH~ C (CH,)~ CH= CHCO~ C (CH~)~ reacted with cyclopentadienylmagnesium chloride at 0" C to yield the alkylated cyclopentadiene, which on heating at 75" C underwent a Diels-Alder reaction to give an ...

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