Bulletin of the Chemical Society of Japan p. 1954 - 1956 (1987)
Update date:2022-08-05
Topics:
Inoue, Yoshiharu
Hydroboration of 5-vinyl-2-norbornene (1) with 9-BBN mainly affords 5-(2-hydroxyethyl)-2- norbornene (2).The iodo ether cyclization of 2 can convert only endo-5-(2-hydroxyethyl)-2-norbornene (2b) to iodo ether 10, followed by reductive elimination and subsequent dehydration to furnish endo-5-vinyl-2-norbornene (1b) which has not been isolated in pure form.Meanwhile, unreacted exo-5-(2-hydroxyethyl)-2-norbornene (2a) produces exo-5-vinyl-2-norbornene (1a) via dehydration.
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Doi:10.1246/cl.1987.1095
(1987)Doi:10.1080/10426500701641262
(2008)Doi:10.1016/j.inoche.2007.10.001
(2008)Doi:10.1002/jlcr.878
(2004)Doi:10.1016/j.bmcl.2013.11.057
(2014)Doi:10.1016/S0968-0896(98)00050-9
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