Oxacyclopropanes synthesis

Bromoalcohol A transforms rapidly in the presence of sodium hydroxide to give the corresponding oxacyclopropane, whereas its diastereomer B does not. Why [Caution Unlike the previous problem, both substrates are frans-bromoalcohols. Hint Draw the most stable cyclohexane chair conformers of both isomers (Section 4-4) and picture the respective transition states for the intramolecular Williamson ether synthesis.]... 

The antibiotic fosfomycin works by interfering with bacterial cell-wall synthesis through oxacyclopropane ring opening. Thus, the enzyme crucial for wall construction is deactivated by reaction of the SH group of one of its cysteine amino acids (for structure, see Problem 45 of Chapter 2) with the strained ether function. 

Halogens are just one of many electrophile-nucleophile combinations that add to alkene double bonds. In this section we begin a survey of some of the most important of these processes, beginning with addition of halogens (the electrophile source) in the presence of water (the nucleophile). The products, 2-haloalcohols, commonly known as halohydrins, are widely used in a number of industrial and synthetic applications. In particular, they are important intermediates for the synthesis of oxacyclopropanes (epoxides. Section 9-9). 

Vicinal haloalcohols undergo intramolecular ring closure in the presence of base to give oxacyclopropanes (Section 9-9) and are therefore useful intermediates in organic synthesis. 

OXACYCLOPROPANE (EPOXIDE) SYNTHESIS EPOXIDATION BY PEROXYCARBOXYLIC ACIDS... 

Outline a short synthesis of tra s-2-methylcyclohexanol from cyclohexene. (Hint Review the reactions of oxacyclopropanes in Section 9-9.)... 

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