Rearrangement of 2-Quinolyl- and 1-Isoquinolylcarbenes to Naphthylnitrenes

Journal of Organic Chemistry

Volumn 69, Issue 6, 2004, Pages 2033-2036

  Lân, Nguyen Mong ^a,b   Burgard, Riko ^a   Wentrup, Curt ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ACTIVATION; DIMERS; ISOMERIZATION; PHOTOLYSIS;

FLASH VACUUM THERMOLYSIS (FVT); RING CONTRACTION REACTIONS;

NITROGEN COMPOUNDS;

1 (5 TETRAZOLYL)ISOQUINOLINE; 1 DIAZOMETHYLISOQUINOLINE; 1 ISOQUINOLYLCARBENE; 1 NAPHTHYLAZIDE; 1 NAPHTHYLNITRENE; 2 (5 TETRAZOLYL)QUINOLINE; 2 CYANOINDENE; 2 DIAZOMETHYLQUINOLINE; 2 NAPHTHYLAZIDE; 2 NAPHTHYLNITRENE; 2 QUINOLYLCARBENE; 3 CYANOINDENE; AZIDE; CARBENOID; IMINE; INDENE DERIVATIVE; ISOQUINOLINE DERIVATIVE; KETENE DERIVATIVE; NAPHTHALENE DERIVATIVE; NAPHTHYL GROUP; QUINOLINE DERIVATIVE; TRIAZOLO[1,5 A]QUINOLINE; TRIAZOLO[5,1 A]ISOQUINOLINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; VACUUM;

EID: 12144287055     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035670c     Document Type: Article

References (32)

1. (a) Wentrup, C. Top. Curr. Chem. 1976, 62, 173.
2. (b) Wentrup, C. Adv. Heterocycl. Chem. 1981, 28, 231.
3. (c) Platz, M. S. Acc. Chem. Res. 1995, 28, 487.
4. (d) Karney; W. L.; Borden, W. T. Adv. Carbene Chem. 2001, 3, 205.
5. (e) Gritsan, N. P.; Platz, M. S. Adv. Carbene Chem. 2001, 3, 255.
6. Maltsev, A.; Bally, T.; Tsao, M.-L.; Platz, M. S.; Kuhn, A.; Vosswinkel, M.; Wentrup, C. J. Am. Chem. Soc. 2004, 126, 237.
7. Wasserman, E. Prog. Phys. Org. Chem. 1971, 8, 319. Coope, J. A. R.; Farmer, J. B.; Gardner, C. L.; McDowell, C. A. J. Chem. Phys. 1965, 42, 54.
8. Wasserman, E. Prog. Phys. Org. Chem. 1971, 8, 319. Coope, J. A. R.; Farmer, J. B.; Gardner, C. L.; McDowell, C. A. J. Chem. Phys. 1965, 42, 54.
9. Kuzaj, M.; Lüerssen, H.; Wentrup, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 480
10. Wentrup, C. Reactive Molecules; Wiley: Mew York, 1985.
11. Kemnitz, C. R.; Karney, W. L.; Borden, W. T. J. Am. Chem. Soc. 1998, 120, 3499.
12. Finnegan, W. G.; Henry, R. A.; Lofquist, R. J. Am. Chem. Soc. 1958, 80, 3908.
13. Wong, M. W.; Leung-Toung, R.; Wentrup, C. J. Am. Chem. Soc. 1993, 115, 2465.
14. Wentrup, C. Helv. Chim. Acta 1978, 61, 1755.
15. (a) The cyclization of diazomethylazines to triazoloazines can be described as a pseudopericyclic reaction.11b Accordingly, the activation barrier is expected to be low, and as a consequence it is difficult to detect the higher energy diazo compounds in equilibrium with the triazoles.
16. (b) Fabian, W. M. F.; Barkulev, V. A.; Kappe, C. O. J. Org. Chem. 1998, 63, 5801.
17. Absolute energies (HF + ZPE) at the B3LYP/6-31+G* level [B3LYP/6-31G* values in brackets]: 3-cyanoindene, -439.884367 [-439.868193] hartree; 2-cyanoindene, -439.887047 [-439.870795] hartree. Full computational data for the cyanoindenes and the transition states TS1-TS4 for their interconversion are given in the Supporting Information
18. Wentrup, C.; Crow, W. D. Tetrahedron 1970, 26, 3965. Wentrup, C.; Crow, W. D. Tetrahedron 1971, 27, 880.
19. Wentrup, C.; Crow, W. D. Tetrahedron 1970, 26, 3965. Wentrup, C.; Crow, W. D. Tetrahedron 1971, 27, 880.
20. Thétaz, C.; Wentrup, C. J. Am. Chem. Soc. 1976, 98, 1258.
21. Wentrup, C. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1980; Vol. 1, pp 263-319.
22. Addicott, C.; Reisinger, A.; Wentrup, C. J. Org. Chem. 2003, 68, 1470.
23. Addicott, C. Ph.D. Thesis, The University of Queensland, Brisbane, Australia, 2002.
24. (a) Annelated cyclopropenes may connect 23 with 22 and 33 with 32. These are expected to be high energy, shallow minima or transition states.3,18b The same is true of the azirines connecting 22 with 21 and 32 with 31.3
25. (b) Kuhn, A.; Vosswinkel, M.; Wentrup, C. J. Org. Chem. 2002, 67, 9023.
26. 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.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, revision E.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
27. Wentrup, C.; Blanch, R.; Briehl, H.; Gross, G. J. Am. Chem. Soc. 1988, 110, 1874. Kappe, C. O.; Wong, M. W.; Wentrup, C. J. Org. Chem. 1995, 60, 1686. Kuhn, A.; Plüg, C.; Wentrup, C. J. Am. Chem. Soc. 2000, 122, 1945.
28. Wentrup, C.; Blanch, R.; Briehl, H.; Gross, G. J. Am. Chem. Soc. 1988, 110, 1874. Kappe, C. O.; Wong, M. W.; Wentrup, C. J. Org. Chem. 1995, 60, 1686. Kuhn, A.; Plüg, C.; Wentrup, C. J. Am. Chem. Soc. 2000, 122, 1945.
29. Wentrup, C.; Blanch, R.; Briehl, H.; Gross, G. J. Am. Chem. Soc. 1988, 110, 1874. Kappe, C. O.; Wong, M. W.; Wentrup, C. J. Org. Chem. 1995, 60, 1686. Kuhn, A.; Plüg, C.; Wentrup, C. J. Am. Chem. Soc. 2000, 122, 1945.
30. Forster, M. O.; Fierz, H. E. J. Chem. Soc 1907, 1942
31. Abramovitch, R. A.; Takaya, T. J. Org. Chem. 1972, 37, 2022.
32. Hantzsch, A.; Schmiedel, M. Ber. Deutsch. Chem. Ges, 1897, 30, 71.