Journal of Organic Chemistry p. 4083 - 4088 (1992)
Update date:2022-08-05
Topics:
Posner, Gary H.
Nelson, Todd D.
Kinter, Chris M.
Johnson, Neil
Captodative 3-(tolylthio)-2-pyrone (1) is shown to be reactive as a nucleophilic diene undergoing 2 + 4-cycloadditions with various electrophilic alkenes under sufficiently mild thermal conditions (= 90 deg C) so that the initial bicyclic lactone adducts can be isolated on gram scale in moderate to very good yields (42-82percent) without loss of CO2.These bicyclic adducts are formed regiospecifically and often with excellent stereoselectivity.These Diels-Alder cycloadditions are the first examples of a captodative unsturated sulfide acting as an enophile.NMR data ((13)C) are presented correlating the electron density in the pyrone diene systems with their Diels-Alder reactivity, and some transformations of the bicyclic lactone adducts are shown to illustrate the value and versatility of these richly functionalized synthetic intermediates.
View MoreHe Bei Shun Er Chemical Co., LTD.
Contact:86-0311-86996932/86860168
Address:No 18,North street
Evergreen Chemical Industry Ltd.
Contact:86-553-4918210
Address:6#2-602 Wanhaobailing
Contact:+36(21)2523420
Address:Head office: 1102 Budapest, SZENT LASZLO TER 24/B. 1/1., HUNGARY / CHINA
Qida Chemical Co., Ltd.(expird)
Contact:+86-25-8776 0031
Address:3-2001 Jiaye Int'l Town, 158 Lushan Road,Nanjing, 210019, China
Contact:+49-4101-3053-0
Address:Waldhofstrasse 14 ,25474 Ellerbek Germany
Doi:10.1039/c2ob26614h
(2012)Doi:10.1021/jo302309m
(2013)Doi:10.1016/j.catcom.2012.09.018
(2012)Doi:10.1021/jo402120w
(2013)Doi:10.1002/cbdv.201200308
(2012)Doi:10.1016/j.molstruc.2012.09.078
(2013)