Journal of Organic Chemistry p. 314 - 320 (1986)
Update date:2022-08-04
Topics:
Katada, Tomonori
Eguchi, Shoji
Sasaki, Tadashi
Thermal cycloaddition reactions of adamantanethione (1) with conjugated dienes such as cyclopentadiene, 2,3-dimethyl-1,3-butadiene, piperylene, isoindole, and isobenzofuran occured smoothly at 20-110 deg C to afford <4 + 2> cycloadducts (3a, 3b, 3d, 23a, and 23b) in good yields.On the other hand, similar treatment of 1 with isoprene gave a 45:55 mixture of regioisomers 3e and 4e.Furthermore, reaction of 1 with Danishefsky's diene (2f) occurred at 110 deg C to afford regioselectively adamantane-2-spiro-(2'-thiacyclohex-5'-en)-4'-one (9) in a good yield after desilylative elimination of the initial adduct.On the other hand, reaction of thiobenzophenone (11) with 2f gave 2,2-diphenyl-6-methoxythiacyclohexan-4-one (14) and 2,2-diphenylthiacyclohex-3-en-5-one (17) in 16percent and 52percent yields, respectively.The nature of these cycloadditions is discussed on the basis of FMO and steric effects.
View MoreContact:027-87677569
Address:Room 2203, yujingmingmen Buidling One, xiongchu Road, wuhan city, hubei province, China
Tianjin Boron PharmaTech Co.,Ltd.(expird)
Contact:86-022-59845187
Address:B9-401, Tianda Science Park,No.80,4th Avenue,TEDA,Tianjin, China
Xinjiang Fufeng Biotechnologies Co., Ltd.
Contact:+86-539-7287111
Address:GANQUANPU INDUSTRIAL PARK, ECONOMIC AND TECHNOLOGICAL DEVELOPMENT AREA (TOUTUNHE DISTRICT) OF URUMQI
Contact:+86-22-83718541
Address:32th Floor, Rongqiao Center Intersection of Changjiang Road and Nankai Six Road Nankai District Tianjin 300102, China
Contact:0571-86821378 ,86820258,56836287,56830923,
Address:Block D ,20F, Tianyuan Building,No.508, Wensan RD, 310013,Hangzhou Zhejiang China
Doi:10.1016/j.bmc.2005.04.009
(2005)Doi:10.1016/0022-328X(91)80157-F
(1991)Doi:10.1021/jo3027438
(2013)Doi:10.1021/ic400150f
(2013)Doi:10.1021/ma302424u
(2013)Doi:10.1016/j.bioorg.2020.103720
(2020)