TY - JOUR
T1 - Addition of hydrogen halides to alkylidenecyclopropanes
T2 - A highly efficient and stereoselective method for the preparation of homoallylic halides
AU - Siriwardana, Amal I.
AU - Nakamura, Itaru
AU - Yamamoto, Yoshinori
PY - 2003/1/27
Y1 - 2003/1/27
N2 - The reaction of alkylidenecyclopropanes with HCl or with HBr proceeds very smoothly at 120°C to produce the corresponding homoallylic halides stereoselectively in good to excellent yields. For example, the reaction of (1-phenylbenzylidene)cyclopropane, (1-butylpentylidene)cyclopropane and octylidenecyclopropane with hydrochloric acid produced the corresponding homoallylic chlorides, 4-chloro-1,1-diphenyl-1-butene, 4-butyl-1-chloro-3-octene and (E)-1-chloro-3-undecene in 99, 96, and 87% yields, respectively. The reaction of (1-butylpentylidene)cyclopropane with hydrobromic acid yielded 1-bromo-4-butyl-3-octene in 95% yield.
AB - The reaction of alkylidenecyclopropanes with HCl or with HBr proceeds very smoothly at 120°C to produce the corresponding homoallylic halides stereoselectively in good to excellent yields. For example, the reaction of (1-phenylbenzylidene)cyclopropane, (1-butylpentylidene)cyclopropane and octylidenecyclopropane with hydrochloric acid produced the corresponding homoallylic chlorides, 4-chloro-1,1-diphenyl-1-butene, 4-butyl-1-chloro-3-octene and (E)-1-chloro-3-undecene in 99, 96, and 87% yields, respectively. The reaction of (1-butylpentylidene)cyclopropane with hydrobromic acid yielded 1-bromo-4-butyl-3-octene in 95% yield.
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U2 - 10.1016/S0040-4039(02)02722-3
DO - 10.1016/S0040-4039(02)02722-3
M3 - Article
AN - SCOPUS:0037467850
SN - 0040-4039
VL - 44
SP - 985
EP - 987
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 5
ER -