Photolysis of 11-methylenepentacyclo[5.4.0.02,6.03,10.05,9]undecan-8-spiro-3′-diazirine.: Medium dependent reaction

被引：0

作者：

Mlinaric-Majerski, K ^{[1
]}

Veljkovic, J ^{[1
]}

Kaselj, M ^{[1
]}

机构：

[1] Rudjer Boskovic Inst, HR-10002 Zagreb, Croatia

来源：

CROATICA CHEMICA ACTA | 2000年 / 73卷 / 02期

关键词：

cage compounds; diazirine; azines; carbenes;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

11-Methylenepentacyclo[5.4.0.0(2,6). 0(3,10).0(5,9)]undecan-8-spiro-3'-diazirine (1) has been synthesized and its photochemical decomposition in different media has been investigated. Irradiation of Nz-purged benzene solution of diazirine 1 produced a mixture of four azine-isomers 7a-d. However, photolysis of 1 in pentane gave a mixture of hydrocarbons 6 as the main insertion products and traces of 1,3-bishomopentaprismane (5). The photolytic decomposition of 1 in N-2-matrix at -196 degrees C proved the formation of diazo-compound 8, which upon warm-up gave traces of 1,3-bishomopentaprismane (5).

引用

页码：575 / 584

页数：10

共 16 条

[1] LEWIS ACID PROMOTED REACTIONS OF 11-METHYLENEPENTACYCLO[5.4.0.02,6.03,10.05,9]UNDECAN-8-ONE AND PENTACYCLO[5.4.0.02,6.03,10.05,9]UNDECAN-8-ONE WITH ETHYL DIAZOACETATE
MARCHAND, AP
REDDY, SP
RAJAPAKSA, D
REN, CT
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11): : 3493 - 3498
[2] ENANTIOSELECTIVE MICROBIAL ASYMMETRIC REDUCTIONS OF CAGE KETONES - PENTACYCLO[5.4.0.02,6.03,10.05,9]UNDECANE-8,11-DIONE AND PENTACYCLO[5.4.0.02,6.03,10.05,9]UNDECAN-8-ONE
MARCHAND, AP
REDDY, GM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 242 - ORGN
[3] STUDIES ON THE FLASH VACUUM PYROLYSIS AND ANOMALOUS COURSE OF ALKALI-METAL PROMOTED REDUCTIONS OF 8-METHYLENEPENTACYCLO[5.4.0.02,6.03,10.05,9]UNDECAN-11-ONE
MEHTA, G
KOTHA, S
MARCHAND, AP
KAYA, R
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (20): : 3848 - 3852
[4] Synthesis of Alkyne and Alkene Ketal Derivatives of Pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8-11-dione and 1-Phenyl-pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8-11-dione
Marx, Frans T. I.
Jordaan, Johan H. L.
Nel, Marike
Vosloo, Hermanus C. M.
SOUTH AFRICAN JOURNAL OF CHEMISTRY-SUID-AFRIKAANSE TYDSKRIF VIR CHEMIE, 2013, 66 : 265 - 269
[5] 11-{[2-(3-Fluorophenyl)ethyl](methyl)amino}pentacyclo[5.4.0.02,6.03,10.05,9]undecan-8-one
Banister, Samuel D.
Clegg, Jack K.
Hanani, Raphy
Kassiou, Michael
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O2693 - U1662
[6] 8-(Biphenyl-4-yl)-8-hydroxypentacyclo-[5.4.0.02,6.03,10.05,9]undecan-11-one ethylene ketal
Boyle, Grant A.
Govender, Thavendran
Kruger, Hendrik G.
Maguire, Glenn E. M.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O283 - U5175
[7] SYNTHESIS AND PHOTOPHYSICAL PROPERTIES OF SOME ENDO-6-SUBSTITUTED NORCAMPHORS AND PENTACYCLO[5.4.0.02,6.03,10.05,9]UNDECAN-8-ONES
SAUERS, RR
ZAMPINO, M
STOCKL, M
FERENTZ, J
SHAMS, H
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (11): : 1862 - 1866
[8] exo-8,exo-11-Diallylpentacyclo-[5.4.0.02,6.03,10.05,9]undecane-endo-8,endo-11-diol
Boyle, Grant A.
Govender, Thavendran
Karpoormath, Rajshekhar
Kruger, Hendrik G.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O4797 - U5875
[9] SYNTHESIS OF (D3)-TRIS-HOMOCUBAN-4-OL VIA CARBENIUM ION REARRANGEMENT OF PENTACYCLO[5.4.0.02,6.03,10.05,9]UNDECAN-8-OL
DEKKER, TG
OLIVER, DW
SOUTH AFRICAN JOURNAL OF CHEMISTRY, 1979, 32 (02) : 45 - 48
[10] SYNTHESES OF PENTACYCLO[6.3.0.02,6.03,10.05,9]UNDECANE-4,7,11-TRIONE (D3-TRISHOMO-CUBANETRIONE) AND PENTACYCLO[5.4.0.02,6.03,10.05,9]UNDECANE-4,8,11-TRIONE
MARCHAND, AP
SHARMA, GVM
PEDNEKAR, PR
ANNAPURNA, GS
CHOU, TC
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1986, 192 : 103 - ORGN

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