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C15H10 and C15H12 Thermal Chemistry: Phenanthrylcarbene Isomers and Phenylindenes by Falling Solid Flash Vacuum Pyrolysis of Tetrazoles
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2015-06-26 00:00:00 , DOI: 10.1021/acs.joc.5b01007 Curt Wentrup 1, 2 , Jürgen Becker 1 , Manfred Diehl 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2015-06-26 00:00:00 , DOI: 10.1021/acs.joc.5b01007 Curt Wentrup 1, 2 , Jürgen Becker 1 , Manfred Diehl 1
Affiliation
2-Phenyl-5-(phenylethynyl)tetrazole 44 provides a new entry to the C15H10 energy surface. Flash vacuum pyrolysis of 44 using the falling solid flash vacuum pyrolysis (FS-FVP) method afforded cyclopenta[def]phenanthrene 31 and cyclopenta[jk]fluorene 52 as the principal products. The products are explained in terms of the formation of N-phenyl-C-phenylethynylnitrile imine/(phenylazo)(phenylethynyl)carbene 45 and its cyclization to 3-(phenylethynyl)-3H-indazole 46b. Pyrolytic loss of N2 from 46b generates C15H10 intermediate 48. Cyclization of 48 to a dibenzocycloheptatetraene derivative and further rearrangements with analogies in the chemistry of phenylcarbene and the naphthylcarbenes leads to the final products. Similar pyrolysis of 2-phenyl-5-styryltetrazole 43 afforded 3-styrylindazole 58, which on further pyrolysis eliminated N2 to generate 3- and 2-phenylindenes 61 and 62 via C15H12 intermediates.
中文翻译:
C 15 H 10和C 15 H 12热化学:四唑的固体闪蒸真空热解法制的菲基卡宾异构体和苯茚
2-苯基-5-(苯基乙炔基)四唑44为C 15 H 10能量表面提供了新的入口。使用降落固体闪蒸热解法(FS-FVP)的闪蒸真空热解法44提供了环戊五[ def ]菲31和环戊[ jk ]芴52作为主要产物。该产品在地层的来解释N-苯基Ç -phenylethynylnitrile亚胺/(苯偶氮基)(苯基乙炔基)卡宾45和它的环化3-(苯基乙炔基)-3- H-吲唑46B。N 2的热解损失从46b中产生C 15 H 10中间体48。将48环化成二苯并环庚二烯衍生物,并进一步类似于苯卡宾和萘基卡宾的化学反应进行重排,得到最终产物。2-苯基-5-苯乙烯基噻唑43的类似热解得到3-苯乙烯基吲唑58,其进一步热解消除了N 2以经由C 15 H 12中间体产生3-和2-苯基茚61和62。
更新日期:2015-06-26
中文翻译:
C 15 H 10和C 15 H 12热化学:四唑的固体闪蒸真空热解法制的菲基卡宾异构体和苯茚
2-苯基-5-(苯基乙炔基)四唑44为C 15 H 10能量表面提供了新的入口。使用降落固体闪蒸热解法(FS-FVP)的闪蒸真空热解法44提供了环戊五[ def ]菲31和环戊[ jk ]芴52作为主要产物。该产品在地层的来解释N-苯基Ç -phenylethynylnitrile亚胺/(苯偶氮基)(苯基乙炔基)卡宾45和它的环化3-(苯基乙炔基)-3- H-吲唑46B。N 2的热解损失从46b中产生C 15 H 10中间体48。将48环化成二苯并环庚二烯衍生物,并进一步类似于苯卡宾和萘基卡宾的化学反应进行重排,得到最终产物。2-苯基-5-苯乙烯基噻唑43的类似热解得到3-苯乙烯基吲唑58,其进一步热解消除了N 2以经由C 15 H 12中间体产生3-和2-苯基茚61和62。