Cyclopropanes with other reactive groups

The oxygen as heteroatom in ethers or carbonyl compounds is weak to moderate Lewis base. Nevertheless, a highly reactive metal carbene complex can interact with the oxygen to generate oxygen ylide. The interaction between ether and metal carbene functional groups is believed to be rather weak as demonstrated by the facts that other metal carbene reactions, such as G-H insertion and cyclopropanation, can proceed in ethereal solvents." These experiments demonstrate that the formation of the metal ylide is much less favored in the equilibrium shown in Equation (1). ... 

Cyclopropanols can be converted to various cyclopropyloxy derivatives (esters, e.g. acetates, ethers, e.g. methyl and ethyl ethers, and acetals, e.g. tetrahydropyran-2-yloxy derivatives) under the appropriate reaction conditions. In most cases the synthesis of cyclopropyl esters by the reaction between a cyclopropanol and an acid chloride (e.g. formation of 1 ) or acetic anhydride (e.g. formation of 2 ) have been reported. The yields were particularly good (84-95%) when acetic anhydride was used, although a drawback of the reaction can be byproduct formation. When a reactive moiety is attached to the cyclopropane ring in addition to the hydroxy group, other reactions can also occur m-l-(aminomethyl)-2,2-dimethyl-3-(2-methylprop-l-enyl)cyclopropanol (3) reacted with phosgene in benzene to give the corresponding carbamate l,l-dimethyl-2-(2-methylprop-l-enyl)-4-oxa-6-azaspiro[2.4]heptan-5-one (4) in 31% yield. ... 

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