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 MoreChuzhou Baiao Biologhy S&T Co., Ltd.
Contact:+86-25-83212599；+86-25-83212699 13705185959
Address:Room 905, Tianzheng International Platza, No.399, Zhongyang Road ,Nanjing, Jiangsu Province, China
Contact:+1-973-357-0577
Address:10 Taft Rd.
Jinhua City Mingzhu Pharmaceutical Co.,Ltd.
Contact:15857995878 0579-82207761
Address:No.169 Shenze Road, New Area,Jinpan Development Zone, Jinhua
Contact:852-27701081
Address:Room 2509, New Tech Plaza, 34 Tai Yau St., San Po Kong, HK
Reliable Pharma Technology (Shanghai) Co., Ltd.
Contact:0086-21-67676847-8008
Address:Lane 1500, No.68, Xinfei Road, Songjiang District, Shanghai, 201611, P.R.China.
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)
