Efficient preparation of vinylcyclopropane by S(N') cyclization of the organolithium derived from (E)5-iodo-1-methoxy-2-pentene

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6157-6158

  Bailey, William F ^a   Tao, Yong ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; IODIDE; ORGANOLITHIUM COMPOUND;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS;

EID: 0030818648     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01423-8     Document Type: Article

References (17)

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3. Chamberlin, A. R.; Bloom, S. H.; Cervini, L. A.; Fotsch, C. H. J. Am. Chem. Soc. 1988, 110, 4788.
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8. Anantanarayan, A.; Dutton, P. J.; Fyles, T. M.; Pitre, M. J. J. Org. Chem. 1986, 51, 752.
9. 11OI: C, 31.88; H, 4.90. Found: C, 31.56; H, 4.50.
10. Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404.
11. It might be noted that treatment of allyl methyl ether with an alkyllithium in ethereal solvents leads to abstraction of an allylic proton to give (1-methoxy)allyllithium, see: Evans, D. A.; Andrews, G. C.; Buckwalter, B. J. Am. Chem. Soc. 1974, 96, 5560.
12. 13C chemical shifts are virtually identical to those previously reported for vinylcyclopropane [Rudolph, A.; Weedon, A. Can. J. Chem. 1990, 68, 1590]; viz., δ 6.67, 14.76, 111.50, 142.61
13. (a) Demjanow, N. J.; Dojarenko, M. Chem. Ber. 1922, 55, 2718.
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