Hypervalent iodine-mediated ring contraction of 2- arylidenecycloalkanones: A facile synthesis of 2-arylidenecycloalkane carboxylates

Synthesis

Volumn , Issue 8, 1999, Pages 1288-1290

  Varma, Rajender S ^a   Kumar, Dalip ^a  

^a SAM HOUSTON STATE UNIVERSITY   (United States)

Author keywords

2 arylidenecycloalkanones; 2 arylidenecycloalkane carboxylates; Iodobenzene diacetate; Perchloric acid; Ring contraction; Triethyl orthoformate

Indexed keywords

CYCLOALKANE DERIVATIVE; FORMIC ACID DERIVATIVE; IODINE DERIVATIVE; IODOBENZOIC ACID DERIVATIVE; PERCHLORIC ACID; REAGENT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032843149     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3539     Document Type: Article

References (26)

1. (a) Varvoglis, A. Hypervalent Iodine in Organic Synthesis, Academic Press: London, 1997.
2. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431.
3. (c) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365.
4. (d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
5. (e) Varvoglis, A. Tetrahedron 1997, 53, 1179.
6. (f) Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221.
7. (a) Moriarty, R. M.; Prakash, O.; Freeman, W. A. J. Chem. Soc., Chem. Commun. 1984, 927.
8. (b) Moriarty, R. M.; Khosrowshahi, J. S.; Prakash, O. Tetrahedron Lett. 1985, 26, 2961.
9. (c) Reberovic, L.; Koser, G. F. J. Org. Chem. 1984, 49, 2462.
10. (d) Singh, O. V.; Garg, C. P.; Kapoor, R. P. Synthesis 1990, 1025.
11. (a) Bindra, J. S. In The Total Synthesis of Natural Compounds; Apsimon, J. Ed.; Wiley: New York, 1981; Vol 4, p 353.
12. (b) Kobayashi, Y.; Tsuji, J. Tetrahedron Lett. 1981, 22, 4295.
13. (c) Boeckman, R. K.; Naegely, P. C.; Arthur, S. D. J. Org. Chem. 1980, 45, 754.
14. (a) Mathew, F.; Myrboh, B. Molecules 1996, 1, 79.
15. (b) Angoh, A. G.; Clive, D. L. J. J. Chem. Soc., Chem. Commun. 1985, 980.
16. (c) Bubnov, Y. N.; Larinovich, L. I. Tetrahedron Lett. 1985, 26, 4551.
17. (d) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1.
18. (d) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1.
19. (e) Curran, D.P.; Chen, M. H. J. Am. Chem. Soc. 1987, 109, 6558.
20. (f) Cekovic, Z.; Cvetkovic, M. Tetrahedron Lett. 1980, 21, 2675.
21. (a) Varma, R. S.; Saini, R. K.; Dahiya, R. Tetrahedron Lett. 1997, 38, 7029.
22. (b) Prakash, O.; Saini, R. K.; Singh, S. P.; Varma, R. S. Tetrahedron Lett. 1997, 38, 3147.
23. (c) Varma, R. S.; Saini, R. K.; Dahiya, R. J. Chem. Res (S) 1998, 120.
24. (d) Varma, R. S.; Kumar, D. Tetrahedron Lett. 1998, 39, 9113.
25. (e) Varma, R. S.; Kumar, D. J. Heterocycl. Chem. 1998, 1533.
26. Bultzly, R.; Lorz, E.; Russell, P. B.; Smith, F. M. J. Am. Chem. Soc. 1955, 7, 624.