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• 39819-74-4 3-methoxycyclopent-1-ene 
• 78522-01-7 (2R,3R)-2-Bromo-3-methoxy-cyclopentanol 

Relevant academic research and scientific papers

Chemo- and diastereoselectivities in the oxidation of cyclopentenols with dimethyldioxirane and methyl(trifluoromethyl)dioxirane

A comparison of the diastereoselectivity and the chemoselectivity (epoxidation versus allylic oxidation) attained in the oxidation of cyclopentenols using dimethyldioxirane and methyl(trifluoromethyl)dioxirane is reported. The results indicate that with both dioxiranes diastereoselective epoxidation of allylic cyclopentenols is accompanied by competitive allylic oxidation to the corresponding enone; for the latter a likely rationale is proposed.

Prostaglandin Endoperoxide Model Compounds. Part 1. Synthesis of (n + 5)-Bromodioxabicycloalkanes

Four cis-(n + 5)-bromodioxabicycloalkanes (12) (n= 2 - 5) have been prepared from C5-C8 cycloalkenes by the sequence singlet oxygenation, bromination, and treatment with silver trifluoroacetate.Photo-oxygenation of cycloalkenes provides a convenient route to the corresponding cycloalk-2-enyl hydroperoxides (6).Bromination of each of these proceeds smoothly in carbon tetrachloride to afford a mixture of cis-2,trans-3-dibromocycloalkyl hydroperoxide (10) and trans-2,cis-3-dibromocycloalkyl hydroperoxide (11).Except for 2,3-dibromocyclo-octyl hydroperoxide, the maior isomer obtained is (10) and the fraction of (10) in the mixture can be increased by silylating (6) with bistrimethylsilylacetamide before bromination and afterwards desilylating the dibromo-adducts by methanolysis.Both (10) and, less efficiently, (11) react with silver trifluoroacetate to give compounds (12), which are readily separated by low-temperature column chromatography from the bromo-trifluoroacetoxy-cycloalkyl hydroperoxides concurrently formed.Configurational assignments for (10), (11) and (12) have been made on the basis of spectroscopic date and chemical reactions.