Thermal and photochemical rearrangements of cyclopropyl ethers of p-quinols. Competing reaction pathways leading to five-and six-membered ring spirocyclic …

TN Biggs, JS Swenton

Index: Biggs, Timothy N.; Swenton, John S. Journal of Organic Chemistry, 1992 , vol. 57, # 21 p. 5568 - 5573

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Citation Number: 10

Abstract

Cyclopropyl ethers of p-quinols were prepared by reaction of 3”-methylenedispiro [1, 3- dioxolone-2, 1'-[2, 5]-cyclohexadiene-4', 1”(3” H)-isobenzofuran] and the associated ketone with ethyl diazoacetate/rhodium (II) acetate and diethylzinc/methylene iodide, respectively, and their thermal and photochemical rearrangements were studied. One major process at 180-200 OC is cleavage of the carbon-oxygen bond at the spiro center of the quinol to ...