Geminate-substituted cyclopentadienes. 1. Synthesis of 5, 5-dialkylcyclopentadienes via 4, 4-dialkylcyclopent-2-en-1-ones

RW Holder, JP Daub, WE Baker…

Index: Holder, Richard W.; Daub, John P.; Baker, Wesley E.; Gilbert, Raymond H; Graf, Norman A. Journal of Organic Chemistry, 1982 , vol. 47, # 8 p. 1445 - 1451

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Citation Number: 27

Abstract

A synthetic route for the preparation of 5, 5-dialkylcyclopentdienes (1) via 4, 4- dialkylcyclopent-2-en-l-ones (3) is described. Beginning with ketones (in which the two carbonyl substituents will become the two alkyl groups in the title compounds), the route traverses the Guareschi imides 5, 3, 3-didkylglutaric acids 4 and their ethyl eaters 7, masked acyloins 8, cyclopentenones 3, alcohols 9, and bromides 10 to reach the dienes 1. ...