Journal of Organic Chemistry p. 1549 - 1556 (1980)
Update date:2022-08-03
Topics:
Mayo, Paul de
Sydnes, Leiv K.
Wenska, Grazyna
Quinoline derivatives are formed in fair to good yields when acetonitrile solutions of o-vinylthioanilides are irradiated with Pyrex-filtered light.The transformation is a singlet reaction and involves intramolecular cycloaddition of the thioamide, yielding unstable thietanes, as the initial step.In the case of o-(1-trans-propenyl)thioacetanilide (2a) the corresponding thietane has been detected by 1H NMR spectroscopy by irradiating a toluene solution of the compound at -78 deg C.The quantum yield of quinoline formation from 2a appeared to be solvent dependent.Concomitant with quinoline formation, triplet cis-trans isomerization of the vinyl moiety takes place.In the case of 2a the quantum yield for trans -> cis isomerization is 0.506.A variable-temperature 1H NMR study of 2,3-dimethylquinoline in toluene solution has also been performed.For the 2,3-dimethylquinoline-toluene complex the enthalpy and entropy of formation are -1.03 +/- 0.10 kcal/mol and -3.7 +/- 0.2 gibbs/mol, respectively.
View MoreContact:Tel:+86-29-88764861 Fax:+86-29-88764861
Address:Rm#2107, Block A, Epin Meidao Building, Gaoxin Rd, Hi-Tech Zone, Xi’an, China
Contact:86-510-82853889
Address:Rm.3732, No.18-2,Yonghe Rd.,Wuxi,Jiangsu,214023,China
QINGDAO HONG JIN CHEMICAL CO.,LTD.
website:http://www.hongjinchem.com
Contact:+86-532-83657313
Address:2ND Building, 8 Shangqing Road, Qingdao, Shandong Province, China.
Huangshi Shennong Chemical Technology Co., Ltd
Contact:+86-714-3072290
Address:Eastern industrial park , Tieshan district , Huangshi city ,Hubei province , China
Nanjing Legend Pharmaceutical & Chemical Co., Ltd.
Contact:+86-25-83767696
Address:14-7 Zhongshan Lu Guluo District, Nanjing
Doi:10.1021/jo01024a014
(1964)Doi:10.1021/ol062093g
(2006)Doi:10.1021/j100238a019
(1983)Doi:10.1016/S0008-6215(00)83674-5
(1980)Doi:10.1021/jo01299a042
(1980)Doi:10.1021/acs.joc.1c00848
(2021)