Periselectivity in the cycloaddition reactions of pentafulvenes with 3-oxidopyrylium betaines: Effect of substituent on the C-6 carbon

Synthesis

Volumn , Issue 12, 2008, Pages 1955-1959

  Krishnan, K Syam ^a   Rajan, Rani ^a   Radhakrishnan, K V ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

Cycloaddition; Oxidopyrylium betaines; Pentafulvenes; Periselectivity

Indexed keywords

ADDITION REACTIONS; CYCLOADDITION;

CYCLOADDITION REACTIONS; PENTAFULVENES;

REACTION KINETICS;

3 OXIDOPYRYLIUM BETAINE DERIVATIVE; ADAMANTANE DERIVATIVE; ADAMANTYLIDENEFULVENE; BETAINE DERIVATIVE; CARBON;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; INFRARED SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 46649092544     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067093     Document Type: Article

References (16)

1. Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991.
2. Krygowski, T. M.; Ciesielski, A. M. Chem. Pap. 1995, 49, 128.
3. Yates, P. Advances in Alicyclic Chemistry, Vol. 2; Academic Press: New York, 1968.
4. (a) Hong, B.-C.; Chen, F.-L.; Chen, S.-H.; Liao, J.-H.; Lee, G.-H. Org. Lett. 2005, 7, 557; and references cited therein.
5. (b) Zhang, X.; Khan, S. I.; Foote, C. S. J. Org. Chem. 1995, 60, 4102.
6. (a) Anas, S.; Sajisha, V. S.; Mohanlal, S.; Radhakrishnan, K. V. Synlett 2006, 2399.
7. (b) Nair, V.; Nair, A. G.; Rahdakrishnan, K. V.; Nandakumar, M. V.; Rath, N. P. Synlett 1997, 767.
8. (c) Nair, V.; Anilkumar, G.; Radhakrishnan, K. V.; Nandakumar, M. V.; Kumar, S. Tetrahedron 1997, 53, 15903.
9. (d) Nair, V.; Jayan, C. N.; Radhakrishnan, K. V.; Anilkumar, G.; Rath, N. P. Tetrahedron 2001, 57, 5807.
10. (a) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3359.
11. (b) Sammes, P. G.; Street, L. J. J. Chem. Soc, Perkin Trans. 1 1983, 2729.
12. (a) Radhakrishnan, K. V.; Krishnan, S. K.; Bhadbhade, M. M.; Bhosekar, G. V. Tetrahedron Lett. 2005, 46, 4785.
13. (b) Krishnan, S. K.; Sajisha, S.; Anas, S.; Suresh, C. H.; Bhadbhade, M. M.; Bhosekar, G. V.; Radhakrishnan, K. V. Tetrahedron 2006, 62, 5952.
14. (c) Krishnan, K. S.; Suresh, E.; Mathew, S.; Radhakrishnan, K. V. Synthesis 2006, 1811.
15. (d) Krishnan, K. S.; Smitha, M.; Suresh, E.; Radhakrishnan, K. V. Tetrahedron 2006, 62, 12345.
16. Hong, B.-C.; Sun, S.-S.; Tsai, Y.-C. J. Org. Chem. 1997, 62, 7717.