Syntheses and pyrolyses of furan analogues of α-Oxo- o -quinodimethanes. Formation of methylenecyclobutenone and 1-buten-3-yne via a vinylcarbene-cyclopropene rearrangement

Journal of Organic Chemistry

Volumn 76, Issue 20, 2011, Pages 8440-8446

  Tseng, Pen Wen ^a   Kung, Chen Yu ^a   Chen, Hsing Yin ^b   Chou, Chin Hsing ^a  

^a NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

^b KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENES; CO MOLECULE; CYCLOPROPENES; FLASH VACUUM; QUINODIMETHANES; RING CONTRACTION; RING OPENING;

AROMATIC COMPOUNDS; DEUTERIUM; ORGANIC POLLUTANTS;

PROPYLENE;

BENZOIC 2 METHYL 3 FUROIC ANHYDRIDE; BENZOIC 3 METHYL 2 FUROIC ANHYDRIDE; CARBENE; CARBON MONOXIDE; FURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ELIMINATION REACTION; ENERGY YIELD; FLASH VACUUM PYROLYSIS; POLYMERIZATION; PYROLYSIS; REACTOR CASCADE; TEMPERATURE DEPENDENCE;

ANHYDRIDES; CHEMISTRY, ORGANIC; CYCLOBUTANES; CYCLOPROPANES; FURANS; MAGNETIC RESONANCE SPECTROSCOPY; METHANE; MOLECULAR STRUCTURE; VINYL COMPOUNDS;

EID: 80054108287     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201743h     Document Type: Article

References (20)

1. Cava, M. P.; Napier, D. R. J. Am. Chem. Soc. 1957, 79, 1701-1705
2. Cava, M. P.; Deana, A. A.; Muth, K. J. Am. Chem. Soc. 1959, 81, 6458-6460
3. Jensen, F. R.; Coleman, W. E. J. Am. Chem. Soc. 1958, 80, 6149
4. For leading references, see: McCullough, J. J. Acc. Chem. Res. 1980, 13, 270-276
5. Spangler, R. J.; Kim, J. H. Tetrahedron 1972, 13, 1249-1251
6. Schiess, P.; Heitzmann, P. Angew. Chem., Int. Ed. Engl. 1977, 16, 469-470
7. Tseng, P. W.; Yet, S. W.; Chou, C. H. J. Org. Chem. 2008, 73, 3481-3485
8. Chou, C. H.; Trahanosky, W. S. J. Am. Chem. Soc. 1986, 108, 4138-4144
9. Sherman, E.; Amstutz, E. D. J. Am. Chem. Soc. 1950, 72, 2195-2198
10. Trahanosky, W. S.; Ong, C. C.; Pataky, J. G.; Weitl, F. L.; Muellen, P. W.; Clardy, J. C.; Hansen, R. S. J. Org. Chem. 1971, 36, 3575-3579
11. Trahanovsky, W. S.; Park, M. G. J. Am. Chem. Soc. 1973, 95, 5412
12. Trahanovsky, W. S.; Park, M. G. J. Org. Chem. 1974, 39, 1448-1449
13. Knight, D. W.; Nott, A. P. J. Chem. Soc., Perkin Trans. 1 1981, 1125-1131
14. Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082-1087
15. Hurd, C. D.; Wilkinson, K. J. Am. Chem. Soc. 1948, 70, 739-741
16. Knight, D. W. Tetrahedron Lett. 1979, 5, 469-472
17. Brown, R. F. C.; Eastwood, F. W.; McMullen, G. L. Aust. J. Chem. 1977, 30, 179-193
18. Aitken, R. A.; Atherton, J. I. J. Chem. Soc., Perkin Trans. 1 1994, 11, 1281-1284
19. Wang, W. S.; Tseng, P. W.; Chou., C. H.; Shiea, J. T. 1998, Rapid Commun. Mass Spectrom. 1998, 12, 931-934.
20. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, J.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02; Gaussian, Inc., Wallingford, CT, 2009.