Decomposition of alkene adducts of thianthrene cation radical in nitrile solvents. Formation of alkyl-2-oxazolines and a new class of four-component products: 5-[(1-alkoxyalkylidene) ammonio]alkylthianthrenium diperchlorates

Journal of Organic Chemistry

Volumn 69, Issue 26, 2004, Pages 9255-9261

  Shine, Henry J ^a   Zhao, Bing Jun ^a   Marx, John N ^a   Ould Ely, Teyeb ^b   Whitmire, Kenton H ^b  

^a TEXAS TECH UNIVERSITY   (United States)

^b RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; AMINO ACIDS; DECOMPOSITION; NITRILE RESINS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS; POSITIVE IONS; X RAY CRYSTALLOGRAPHY;

ADDUCTS; PERCHLORATE SALTS;

OLEFINS;

1,2 (5,10 THIANTHRENIUMDIYL) 2 METHYLPROPANE DIPERCHLORATE; 2 (ACETYLAMINO) 2 METHYLPROPANOL; 2 AMINO 2 METHYLPROPYL ACETATE; 2 METHYL 2 BUTENE; 2 METHYLBUTENE; 2 METHYLPENTENE; 2,4,4 TRIMETHYL 2 OXAZOLINE; ACETONITRILE; ALKENE; DIHEXAFLUOROPHOSPHATE; FLUOROPHOSPHATE; ISOBUTYLENE; NITRILE; OXAZOLINE DERIVATIVE; PERCHLORATE; RADICAL; SOLVENT; THIANTHRENE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DECOMPOSITION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 10844239827     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0402125     Document Type: Article

References (15)

1. Lee, W. K.; Liu, B.; Park, C. W.; Shine, H. J.; Guzman-Jimenez, I. Y.; Whitmire, K. H. J. Org. Chem. 1999, 64, 9206-9210.
2. Qian, D.-Q.; Shine, H. J.; Guzman-Jimenez, I. Y.; Thurston, J. H.; Whitmire, K. H. J. Org. Chem. 2002, 67, 4030-4039.
3. Shine, H. J.; Zhao, B.-J.; Qian, D.-Q.; Marx, J. N.; Guzman-Jimenez, I. Y.; Thurston, J. H.; Ould-Ely, T.; Whitmire, K. H. J. Org. Chem. 2003, 68, 8910-8917.
4. Zhao, W.; Shine, H. J. Can. J. Chem. 1998, 76, 695-702.
5. Kaminski, J. J.; Bodor, N.; Higuchi, T. J. Pharm. Sci. 1976, 65, 1733-1736.
6. Gabriel, S.; Heymann, Th. Chem. Ber. 1890, 23, 2493-2502.
7. Phillips, A. P.; Baltzly, R. J. Am. Chem. Soc. 1947, 69, 200-204.
8. Porter, G. R.; Rydon, H. N.; Schofield, J. A. J. Chem. Soc. 1960, 2686-2690.
9. Meyers, A. I.; Temple, D. L., Jr. J. Am. Chem. Soc. 1970, 92, 6646-6647.
10. Sylvestre, J.; Papantoniou, C. Compt. Rend. 1965, 260, 1440-1441.
11. Nishiwaki, N.; Nishida, D.; Ohnishi, T.; Hidaka, F.; Satoru, S.; Tamura, M.; Hori, K.; Tohda, Y.; Ariga, M. J. Org. Chem. 2003, 68, 8650-8656.
12. Murata, Y.; Shine, H. J. J. Org. Chem. 1969, 34, 3368-3372.
13. Handrick, G. R.; Atkinson, E. R.; Granchelli, F. E.; Bruni, R. J. J. Med. Chem. 1965, 8, 762-766.
14. Hall, G. E.; Hughes, D.; Rae, D.; Rhodes, A. P. Tetrahedron Lett. 1867, 241-246.
15. Newcomb, M.; Varick, T. R.; Goh, S.-H. J. Am. Chem. Soc. 1990, 112, 5186-5193.