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2; Pyrex filter; 2 h photolysis time at 12-15°C.
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Fumaronitrile traps the diazo compound in a 1,3-dipolar cycloaddition, preventing the formation of a carbocation via the diazonium ion route (also see ref 15). In addition to 5 and 6, several products probably stemming from the 1,3-dipolar addition to the diazo compound and decomposition products thereof could be detected. For the photochemical decomposition of 1,3-dipolar addition products see: Sander, W.; Wrobel, R.; Komnick, P.; Rademacher, P.; Muchall, H. M.; Quast, H. Eur. J. Org. Chem. 2000, 91.
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0343537713
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Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defres, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94; Gaussian, Inc.: Pittsburgh, PA, 1995. Tomoda, S., private communication: HF/6-31G*(d). EFOE density of LUMO: syn: 3.1403%, anti: 1.5494%; EFOE Density of HOMO: syn: 1.2625%, anti: 1.7965%; for an overview of the method see: Tomoda, S. Chem. Rev. 1999, 99, 1243; Tomoda, S.; Senju, T. Tetrahedron 1999, 55, 5303.
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Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defres, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94; Gaussian, Inc.: Pittsburgh, PA, 1995. Tomoda, S., private communication: HF/6-31G*(d). EFOE density of LUMO: syn: 3.1403%, anti: 1.5494%; EFOE Density of HOMO: syn: 1.2625%, anti: 1.7965%; for an overview of the method see: Tomoda, S. Chem. Rev. 1999, 99, 1243; Tomoda, S.; Senju, T. Tetrahedron 1999, 55, 5303.
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Tomoda, S.1
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0000745474
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Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defres, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94; Gaussian, Inc.: Pittsburgh, PA, 1995. Tomoda, S., private communication: HF/6-31G*(d). EFOE density of LUMO: syn: 3.1403%, anti: 1.5494%; EFOE Density of HOMO: syn: 1.2625%, anti: 1.7965%; for an overview of the method see: Tomoda, S. Chem. Rev. 1999, 99, 1243; Tomoda, S.; Senju, T. Tetrahedron 1999, 55, 5303.
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Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defres, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94; Gaussian, Inc.: Pittsburgh, PA, 1995. Tomoda, S., private communication: HF/6-31G*(d). EFOE density of LUMO: syn: 3.1403%, anti: 1.5494%; EFOE Density of HOMO: syn: 1.2625%, anti: 1.7965%; for an overview of the method see: Tomoda, S. Chem. Rev. 1999, 99, 1243; Tomoda, S.; Senju, T. Tetrahedron 1999, 55, 5303.
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