Journal of the Chemical Society. Perkin transactions I p. 1119 - 1122 (1986)
Update date:2022-08-03
Topics:
Hickey, Deirdre M. B.
Moody, Christopher J.
Rees, Charles W.
Photolysis of azidocinnamates (1a-e) at 300 nm in light petroleum gives exclusively the triazatricyclononenes (7a-e) in a highly stereospecific trimerisation of the corresponding azirine (2).A mechanism is proposed involving the sequence: azide (1) <*> azirine (2) <*> nitrile ylide (8) <*> dimer (9) <*> azomethine ylide (10) <*> trimer (7) (Scheme 2).This mechanism not only rationalises the formation of the trimers (7), rather than dimers or oligomers, but also their stereochemistry.Further evidence for it is provided by photolyses of the azidocinnamates (1f-h) which give the 'dimer' (13), the cyclopropaisoquinoline (16), and the imidazopyridine (20), respectively; these three products result from intramolecular interception of the azomethine ylide or nitrile ylide intermediates.
View MoreZipont chem(wuhan）Tech co.，Ltd
Contact:+86-27-87587198
Address:wuhan
SHENYANG COMEBOARD TECHNOLOGY CO., LTD
Contact:+86-24-25724626
Address:Room2210,Tianbao International Building,No.8-1 Weigong South Street,Tiexi District,Shenyang,China
Taizhou Sunny Chemical Co.,Ltd
Contact:+86-523-86920899 +86-13951172783
Address:No.11 Xingyuang road, Gaoyong Chemical Industry Park, Gaogang Jiangsu China
website:http://www.lonwinchem.com
Contact:Tel: 86-21-59858395
Address:No#966,Huaxu Road,Shanghai 201702,P.R.China
Jinan Jianfeng Chemical Co., Ltd
Contact:0086-531-88110457
Address:sales01(-a-t-)pharmachemm{dot}c+o+m
Doi:10.1016/S0957-4166(02)00094-0
(2002)Doi:10.1016/S0040-4020(01)93342-3
(1960)Doi:10.1002/ejoc.201901790
(2020)Doi:10.1055/s-0030-1258483
(2010)Doi:10.1016/j.bmc.2008.07.090
(2008)Doi:10.1016/j.tet.2012.01.087
(2012)
