Journal of Organic Chemistry p. 3036 - 3040 (1981)
Update date:2022-08-05
Topics:
Rammash, Bahlul Kh.
Gladstone, C.M.
Wong, John L.
The reaction of the title azadiene 1 with cyclopentadiene via the ene moiety of 1 as the dienophile yielded 5 quantitatively.Chlorination of 5 gave rise to a single dichloro derivative 6.The cycloadduct 7, obtained from reacting cyclopentene with 1, was found to be different from 9, the hydrogenation product of 5, thus eliminating any product which requires 1 behaving as diene.Also, the use of 15N label in the sequence rules out 5a, an imine isomer, as a candidate.However, the existence of the diene character of 1 in reaction with a conjugated diene was found upon heating 1 with cyclohexadiene.Two adducts were isolated in a ratio of 4:1.The minor product was assigned structure 12 which is similar to 5 derived from 1.The cyclohexene adduct of 1 was found to be identical with 14, the dihydro derivative of the major adduct from cyclohexadiene.The latter is assigned structure 10, analogous to the regiospecific formation of endo-5-substituted-2-azanorbornenes from 1 and olefins such as styrene.In the case of an acyclic diene addend such as trans-piperylene, 1 behaves only as a diene, yielding the adduct 16 only.It appears that the steric factor is an important one in deciding the diene or dienophilic reactivity of 1.
View MoreTIANJIN FESTO CHEMICAL CO.,LTD(expird)
Contact:86-22-25814570
Address:No.12th,5th Ave.,TEDA,Tianjin,China
Shanghai Synmedia Chemical Co., Ltd
Contact:+86-21-38681880
Address:6th Floor, 11A Building, No.528 Ruiqing Road, Heqing town, Pudong new district, Shanghai China
Wuhan Chemwish Technology Co., Ltd
website:http://www.chemwish.com/
Contact:+86-27-67849912
Address:Room 1311, Unit 2, Block1, Innovation Road East Lake High-tech Development Zone Wuhan, Hubei,P.R. China
website:http://www.lidepharma.com
Contact:+86-25-58409506
Address:11F, Building A1, No.288 North Zhongshan Road, Gulou District, Nanjing,210003, P.R.China.
Hangzhou Taiyan Trading Co., Ltd(expird)
Contact:+86-13777583958
Address:NO.63, Xingyi Street, Xihu District, Hangzhou, Zhejiang, China
Doi:10.1007/BF00854399
()Doi:10.1002/adsc.201601315
(2017)Doi:10.1080/00397919808003073
(1998)Doi:10.1021/jo01061a021
(1961)Doi:10.1080/00397911.2012.727060
(2013)Doi:10.1016/S0031-9422(00)94534-5
(1986)