Facile Synthesis of beta-Tribromomethyl and Dibromomethylenated Nitroalkanes via Conjugate Addition of Bromoform to Nitroalkenes
DSpace at IIT Bombay
View Archive InfoField | Value | |
Title |
Facile Synthesis of beta-Tribromomethyl and Dibromomethylenated Nitroalkanes via Conjugate Addition of Bromoform to Nitroalkenes
|
|
Creator |
SAHU, B
GURURAJA, GN MOBIN, SM NAMBOOTHIRI, INN |
|
Subject |
electron-poor alkenes
nucleophilic-substitution regioselective synthesis rearrangement haloforms dihalocarbenes derivatives generation catalyst hydrogen |
|
Description |
Addition of bromoform to conjugated nitroalkenes in the presence of Mg provided beta-tribromomethyl nitroalkanes in good to excellent yields and diastereoselectivity. These novel Michael adducts, formed under radical conditions, underwent elimination of HBr in the same pot under reflux to afford beta-dibromomethylenated nitroalkanes in good yield. Alternatively, a one-pot high yielding synthesis of the dibromides was possible under anionic conditions via LDA mediated addition of bromoform to nitroalkenes.
|
|
Publisher |
AMER CHEMICAL SOC
|
|
Date |
2011-07-14T03:32:39Z
2011-12-26T12:47:32Z 2011-12-27T05:36:04Z 2011-07-14T03:32:39Z 2011-12-26T12:47:32Z 2011-12-27T05:36:04Z 2009 |
|
Type |
Article
|
|
Identifier |
JOURNAL OF ORGANIC CHEMISTRY, 74(6), 2601-2604
0022-3263 http://dx.doi.org/10.1021/jo802274q http://dspace.library.iitb.ac.in/xmlui/handle/10054/3848 http://hdl.handle.net/10054/3848 |
|
Language |
en
|
|