TY - JOUR
T1 - Addition of hydrogen halides to alkylidenecyclopropanes: a highly efficient and stereoselective method for the preparation of homoallylic halides
AU - Siriwardana, Amal Inoka
AU - Nakamura, Itaru
AU - Yamamoto, Yoshinori
PY - 2003
Y1 - 2003
N2 - The reaction of alkylidenecyclopropanes with HCl or with HBr proceeds very smoothly at 120degreesC 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. (C) 2003 Elsevier Science Ltd. All rights reserved.
AB - The reaction of alkylidenecyclopropanes with HCl or with HBr proceeds very smoothly at 120degreesC 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. (C) 2003 Elsevier Science Ltd. All rights reserved.
UR - http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6THS-47WBX65-3H-1&_cdi=5290&_user=542840&_pii=S0040403902027223&_orig=search&_coverDate=01%2F
M3 - Article
SN - 0040-4039
VL - 44
SP - 985
EP - 987
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 5
ER -