ISSN:
0570-0833
Keywords:
Cyclopropanes
;
Ethers
;
Cyclopropanes
;
Carbenes
;
Cyclopropyl p-toluenesulfonates
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The reaction of chloromethyl phenyl ether with butyllithium in olefins yields phenoxy-cyclopropanes. 1-Chloro-1-phenoxycyclopropanes can be prepared in a similar manner, though the yields are poor. Alkoxycyclopropanes are formed when dichloromethyl alkyl ethers are treated with methyllithium/lithium iodide in the presence of olefins. Cyclopropanols can be obtained in good yields by reaction of (β-chloroethoxy)cyclopropanes either with butyl- or ethyllithium or with bases. - As was shown by acetolysis experiments with cyclopropyl p-toluenesulfonates having a known steric configuration, the rearrangement of a cyclopropyl derivative into an allyl cation proceeds in accordance with the Woodward-Hoffmann-DePuy rule. The solvolysis of exo-bicyclo[n.1.0]alkyl p-toluene-sulfonates is assumed to proceed via “semi-open” intermediates, which are somewhere between an allyl cation and a cyclopropyl cation.
Additional Material:
7 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/anie.196805881
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