Journal of the Chemical Society. Perkin transactions I p. 1802 - 1806 (1981)
Update date:2022-07-30
Topics:
Horsewood, Peter
Kirby, Gordon W.
Sharma, Ram Prakash
Sweeny, James
Nitrosyl cyanide and 9,10-dimethylanthracene (DMA) (2) reacted at -25 deg C to form the crystallyne cycloadduct, 9,10-dihydro-9,10-(N-cyanoepoxyimino)-9,10-dimethylanthracene (1).The adduct (1) decomposed in the presence of the conjugated diene thebaine (3), to form DMA(2) and the adduct (4) of nitrosyl cyanide and thebaine.First-order kinetics, k = 6.9E-5 s-1, were observed for the release of DMA in benzene at 40 deg C, consistent with slow dissociation of the adduct (1) followed by rapid capture of nitrosyl cyanide by thebain.A similar first-order rate, k = 6.8E-5 s-1, was observed for the reaction of the adduct (1) and triphenylphosphine (2 mol equiv.) under the same conditions, the products being DMA, triphenylphosphine oxide, and triphenylphosphine N-cyanoimide (5).The reactions of nitrosyl cyanide, generated thermally from the adduct (1), were studied with a range of dienes.The conjugated dienes, N-cyanomethyl-N-northebaine (3; NCH2CN replacing NMe), trans,trans-1,4-diphenylbuta-1,3-diene (6; R=H), and ergosteryl acetate (11) all gave the expected cycloadducts (3,6-dihydro-2H-1,2-oxazines).Norbornane gave the tetracyclic adduct (10) arising from 1,4-conjugate addition of nitrosyl cyanide.The reactions of the adduct (1) with tetraphenylcyclopentadienone (14), 1,3-diphenylisobenzofuran (18), 2-methyl-1,3-diphenylisoindole (23), diazofluorene (24), and diphenyldiazomethane all took a more complex course leading in each case to the formation of an N-cyano-ketimine (alkylidene-cyanamide)
View MoreXi'an Costrong Pharmaceutical Co., Ltd.
Contact:029- 68576496
Address:Room 2004,Shuibao Building,No.190,South Erhuan Rd, Yanta District,Xi'an,Shaan Xi,China
Yuan Shi(SuQian)Biotechnology Co.,Ltd
website:http://www.yuanshibio.com
Contact:+86-527-84226672
Address:jiangsu suqian
Zhengzhou Yuanli Biological Technology Co., Ltd.
Contact:+86-371-67897870/67897895
Address:No. 38, Qingyang Street, Zhengzhou, Henan, China
Contact:0086-29-88315623
Address:S711, Innovation Bldg No.25 Gaoxin 1st Rd, Xian P.R of China 710075
Contact:+44 (0)2036089360-31
Address:Chanceryhouse,Chancery Lan
Doi:10.1021/cs400824h
(2013)Doi:10.1021/jo981097z
(1999)Doi:10.1021/ja983222u
(1999)Doi:10.1039/b607342e
(2006)Doi:10.1002/(SICI)1522-2675(19990113)82:1<105::AID-HLCA105>3.0.CO;2-3
(1999)Doi:10.1016/j.jorganchem.2020.121614
(2021)
