Fulvenes acting as 4π components in an intramolecular [4+2] cycloaddition reaction: Entry into the novel 6- oxatricyclo[6.4.0.02,10]dodeca-2,11-diene ring system

Tetrahedron Letters

Volumn 40, Issue 26, 1999, Pages 4869-4870

  Shanmugasundaram, M ^a   Raghunathan, R ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

FULVENE DERIVATIVE; TRICYCLIC AROMATIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; SYNTHESIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0033603573     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00898-9     Document Type: Article

References (13)

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2. Söderberg, B.C.; Austin, L.R.; Davis, C.A.; Nyström, J.; Vågberg, J.O. Tetrahedron 1994, 50, 61, and references cited therein.
3. Hong, B.; Sun, S. Chem. Commun. 1996, 937.
4. Gugelchuk, M.M.; Chan, P.C.; Sprules, T.J. J. Org. Chem. 1994, 59, 7723.
5. Nair, V.; Kumar, S. Tetrahedron 1996, 52, 4029.
6. Wu, T.; Houk, K.N. J. Am. Chem. Soc. 1985, 107, 5308.
7. (a) Muthu, S.; Maruthamuthu, P.; Ragunathan, R.; Vasudeva Rao, P.R.; Mathews, C.K. Tetrahedron Lett. 1994, 35, 1763.
8. (b) Raghunathan, R.; Shanmugasundaram, M; Bhanumathi, S.; Padma Malar, E.J. Heteroatom Chemistry 1998, 327.
9. (c) Shanmugasundaram, M.; Raghunathan, R.; Padma Malar, E.J. Heteroatom Chemistry 1998, 517.
10. (d) Shanmugasundaram, M.; Arulananda Babu, S.; Raghunathan, R.; Padma Malar, E.J. Heteroatom Chemistry 1999, in press.
11. Stone, K.J.; Little, R.D. J. Org. Chem. 1984, 49, 1849
12. To a refluxing solution of fulvenes 2a,b (5 mmol) in 20 ml of nitromethane under nitrogen, lithium perchlorate (5 mmol) was added. After 12h, work up and flash chromatography gave cycloadducts as colourless oils.
13. 13C NMR (100.4 MHz) δ 14.30, 40.63, 48.15, 49.34, 49.41, 60.55, 75.51, 103.44, 122.40, 124.88, 125.79, 126.17, 127.79, 129.20, 130.42, 132.72, 132.95, 136.62, 155.83, 158.24, 173.00.