J. Wrobel, J. Cook
Aug 19, 1980
Citations
0
Influential Citations
6
Citations
Journal
Synthetic Communications
Abstract
Abstract Cyclopentane-1,2-dione 1 has been employed as a synthetic intermediate in the preparation of a variety of organic compounds including propellanes1a, b, iso-coumarones2, and pyrazines3; moreover, the dione 1 shows some promise4 as a potential precursor to the sesquiterpene, modhephene5. Most authors who have reported the synthesis of 1 in recent years have used the method of Acheson, who treated 2-bromocyclopentanone with ferric chloride/water6 and obtained a 40% yield of 1. We required a more efficient preparation of this material and turned to the bromine oxidation7 of the bis-trimethylsilyl ether 2 as a possible alternative. In this regard, diethyl glutarate was cyclized, via the modified acyloin procedure of Bloomfield8, to provide excellent yields of the bis-silyl ether 2; however, treatment of this compound with bromine furnished only small amounts