Journal of Organic Chemistry p. 2472 - 2476 (1983)
Update date:2022-07-29
Topics:
Jahngen, Edwin G. E.
Phillips, Douglas
Kobelski, Robert J.
Demko, Donald M.
The dianion of cyclopropanecarboxylic acid (2) reacted with alkyl halides and deuterated water at temperatures below 0 deg C; however, self-condensation to the β-keto acid 3 was the only observed product at elevated temperatures.This observation contrasts the self-condensation of the ethyl ester where a trimeric diester alcohol is the product.Attempted mixed condensations of the dianion 2 and carboxylic acids without acidic α-protons did not proceed as well, 3 being the major product.Thermal decarboxylation of 3 did not yield the expected dicyclopropyl ketone; rather , a facile rearrangement in a sealed tube at 120 deg C occured, giving rise to 2-cyclopropyl-4,5-dihydrofuran.This "vinyl-cyclopropyl" type rearrangement does not occur through dicyclopropyl ketone or its enolate.
View MoreShanghai Yuanye Bio-Technology Co., Ltd.
website:http://www.shyuanye.com
Contact:+86-21-61845781
Address:Building 6, No. 465, Changta Road,Songjiang District,Shanghai,China
Contact:18710867521(wechat)
Address:Rm10516,Galaxy Tech Building #2,No.25 Tangyan Rd,Hi-Tech Zone,Xi'an, China
Tianjin Tensing Fine Chemical Research Develop Centre
Contact:86-022-23718576,13032267585
Address:2-2-201,13 Guiyuan road,Huayuan Industry district,Tianjin,china
Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd
website:http://www.jlpharms.com
Contact:+86-571-86982636
Address:Rm A606, Fuyi Center, jianqiao street, Jianggan Area
Nantong LiKai Chemical Co.,Ltd
Contact:+86-513-89068669
Address:Jincheng Science Park
Doi:10.1016/j.bmc.2005.01.022
(2005)Doi:10.1016/S0040-4039(00)81427-6
(1983)Doi:10.1016/S0040-4039(00)81349-0
(1983)Doi:10.1016/j.tet.2005.05.057
(2005)Doi:10.1021/jo0505122
(2005)Doi:10.1021/np050074u
(2005)