Journal of the American Chemical Society p. 3112 - 3120 (1981)
Update date:2022-07-30
Topics:
Reich, Hans J.
Shah, Shrenik K.
Gold Paul M.
Olson Richard E.
The reaction of alkyl halides, carbonyl compounds, and trimethylsilyl chloride with the mono- and dianion (1) prepared by deprotonation of phenyl propargyl selenide with lithium diisopropylamide gives 1- or 3-monosubstituted or 1,3-disubstituted propargyl selenides (3a).Oxidation to selenoxides (3b) results in rearrangement to 2-(phenylseleno)-1,3-disubstituted propenones.The rate of rearrangement of propargyl selenoxides increases dramatically when the phenyl group is replaced by a 2-nitrophenyl group, and an intermediate allenyl selenate ester (7c) can be observed by low-temperature NMR.By appropriate modification of oxidation conditions, modest yields of 2-iodopropenes (e.g., 10) or the selenium-free enones or enals can be obtained.A synthesis of (+/-)-7-hydroxymyoporone (15) and its epimer has been carried out by using the dianion 1 to assemble the carbon skeleton.The preparation of α-lithioallenyl phenyl selenide (26) has been accomplished, and its reaction with electrophiles has been studied.
View MoreKA-SHING Business Trade Macau Co., Ltd.
Contact:00853-28430045
Address:23rd Floor, Block 3 La Cite, Areia Preta, Macao
Contact:027-87677569
Address:Room 2203, yujingmingmen Buidling One, xiongchu Road, wuhan city, hubei province, China
RongCheng Tianyu Technology Co.,Ltd.
Contact:86-631-7519595
Address:220Ping Donghai Road RongChengCity,ShangDong Province China
SINO Industries Company Limited(expird)
Contact:86-29-85369724
Address:No.111, Jiefang Road, Xi’an, China
Zhushan County Tianxin Pharmaceutical & Chemical Co., Ltd.
Contact:0086-719-4224892
Address:Tutang Road, Chengguan Town, Zhushan County, Hubei Province
Doi:10.1016/S0040-4039(00)00127-1
(2000)Doi:10.1021/jo0342368
(2003)Doi:10.1016/S0960-894X(03)00475-X
(2003)Doi:10.1055/s-1984-30951
(1984)Doi:10.1039/c5ra05370f
(2015)Doi:10.1016/S0040-4039(00)81621-4
(1983)