Scope and Limitations of Fulvene Syntheses. Preparation of 6-Vinyl-Substituted and-Functionalized Fulvenes. First Examples of Nucleophilic Substitution on a 6-( …

…, A Sadoun, W Smith, G Sheff, M Ossun

Index: Erden, Ihsan; Xu, Fu-Pei; Sadoun, Aladin; Smith, Wyatt; Sheff, Greg; Ossun, Madeleine Journal of Organic Chemistry, 1995 , vol. 60, # 4 p. 813 - 820

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Citation Number: 39

Abstract

Very few 6-vinylfulvenes have previously been reported in the literature. In a few cases where Little's procedure (using pyrrolidine as base) has been employed, most enones undergo conjugate attack by the cyclopentadienyl anion followed by either a retroaldol reaction or dihydropentalene formation. In several cases, Diels-Alder reaction of the enone with cyclopentadiene occurs rather than condensation. We have found that in cases ...