84333-74-4Relevant academic research and scientific papers
Synthesis of Imido-Substituted 3,8-Diphenyl-1,2-diazacycloocta-2,4,6,8-tetraenes and Their Thermolysis
Yogi, Seiichi,Hokama, Kozo,Takayoshi, Sadamori,Tsuge, Otohiko
, p. 731 - 736 (2007/10/02)
Nucleophilic substitution of 4,7-dichloro-3,8-diphenyl-1,2-diazociane with succinimide, phthalimide, N-methyl-p-toluenesulfonamide, and o-benzosulfimide, in the presence of silver oxide, gave the corresponding 4-mono(imido)- and 4,7-di(imido)-1,2-diazocines. 4-Acetoxy-7-phthalimido- and 4-phenylthio-7-phthalimido-1,2-diazocine were also prepared.Thermolysis of the mono(imido)-1,2-diazocines in xylene under reflux afforded the corresponding di(imido)-1,2-diazocine and/or five pyridine derivatives, whose relative yields depended upon the nature of imido substitutents in the diazocines.However, 4,7-di(imido)-1,2-diazocines did not decompose in xylene under reflux.Thermolysis of 4,7-bis(phthalimido)-1,2-diazocine at 300-310 deg C gave 3,6-bis(phthalimido)-2-phenylpyridine with the extrusion of benzonitrile.In the thermolysis of the acetoxy- (230-240 deg C) or phenylthio-substituted 1,2-diazocine (240-260 deg C), 6-acetoxy- and 6-benzoyl-3-phthalimido-2-phenylpyridine, or 6(and 3)-phenylthio-3(and 6)-phthalimido-2-phenylpyridines were isolated together with benzonitrile, respectively.The feature of thermolysis was also discussed.
Preparation of Arylsulfonyl-Substituted 3,8-Diphenyl-1,2-diazacycloocta-2,4,6,8-tetraenes and Their Thermolysis
Yogi, Seiichi,Hokama, Kozo,Tsuge, Otohiko
, p. 343 - 348 (2007/10/02)
Nucleophilic substitution of 4,7-dichloro-3,8-diphenyl-1,2-diazocine with benzenesulfinate gave stable 7-chloro-4-phenylsulfonyl- and 4,7-bis(phenylsulfonyl)-1,2-diazocine.The 4-mono(arylsulfonyl)- and 4,7-bis(arylsulfonyl)-1,2-diazocines were obtained by oxidation of the corresponding mono(arylthio)- and bis(arylthio)-1,2-diazocines, respectively. 4-Phenylsulfonyl-7-phenylthio-1,2-diazocine was also prepared.Thermolysis of all the diazocines gave only pyridine derivatives, and the feature of the thermolysis was also described.
Novel Ring Contraction of 1,2-Diazocine System. Hydrolysis of 7-Substituted 4-Acetoxy- and 4-Phthalimido-3,8-diphenyl-1,2-diazocines Leading to the Formation of Pyrazoles
Yogi, Seiichi,Hokama, Kozo,Tsuge, Otohiko
, p. 157 - 160 (2007/10/02)
A novel ring contraction of 1,2-diazocine system to pyrazoles via bicyclic intermediates has been demonstrated by hydrolysis of 7-substituted 4-acetoxy- and 4-phthalimido-3,8-diphenyl-1,2-diazocines.
Synthesis of Stable 1,2-Diazocines, 4,7-Disubstituted 3,8-Diaryl-1,2-diazacycloocta-2,4,6,8-tetraenes and Their Thermolysis
Yogi, Seiichi,Hokama, Kozo,Ueno, Kazunori,Tsuge, Otohiko
, p. 1087 - 1094 (2007/10/02)
Stable 1,2-diazocines, 3,8-diaryl-4,6-dichloro-1,2-diazacycloocta-2,4,6,8-tetraenes, were prepared via a chlorination-dehydrochlorination sequence starting from readily-available 3,8-diaryl-1,2-diazacycloocta-2,4-dienes.When reacted with metal caroxylates in benzene under reflux, the dichloro-1,2-diazocines were converted into stable 4-acyloxy- and/or 4,7-is(acyloxy)-1,2-diazocines.On the thermolysis in toluene under reflux, all the diazocines gave only pyridine derivatives with extrusion of the corresponding benzonitriles.The thermal behavior of the diazocines are also discussed.
A STABLE 1,2-DIAZOCINE SYSTEM: 3,8-DIPHENYL-1,2-DIAZACYCLOOCTA-2,4,6,8-TETRAENES
Yogi, Seiichi,Hokama, Kozo,Tsuge, Otohiko
, p. 1579 - 1582 (2007/10/02)
Stable 1,2-diazocines, 3,8-diphenyl-1,2-diazacycloocta-2,4,6,8-tetraenes, were prepared via halogenation-dehydrohalogenation sequences starting from readily available 3,8-diphenyl-1,2-diazacycloocta-2,8-diene.Thermolysis and photolysis of the 1,2-diazocines are also described.
