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The chemistry of small ring compounds. Part 44. Solvolysis of cyclopropyl sulfides and ethers

1981; Royal Netherlands Chemical Society; Volume: 100; Issue: 5 Linguagem: Inglês

10.1002/recl.19811000506

1878-7096

R. Jorritsma, H. Steinberg, Th. J. de Boer,

Organic Chemistry Cycloaddition Reactions

Abstract 1‐Chlorocyclopropyl methyl ether and the corresponding sulfide are methanolysed without any rupture of the three‐membered ring. The solvolysis of 1‐halocyclopropyl sulfides has been studied kinetically and takes place via an S N 1 mechanism. Methyl substituents in the cyclopropyl ring promote ring opening. This, and the effect of variation of the leaving group (Cl, Br, SMe 2 ⊕ ), can be rationalised in terms of relative stabilities of intermediary substituted cyclopropyl and alkyl cations.