A one step conversion of sulfoxides to aldehydes by the neighboring group participation in the pummerer rearrangement of ortho-hydroxymethyl aryl benzyl sulfoxides

Heterocycles

Volumn 46, Issue 1, 1997, Pages 177-184

  Naka, Hiroyuki ^a   Sato, Soichi ^a   Horn, Ernst ^a   Furukawa, Naomichi ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343154677     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s67     Document Type: Article

References (13)

1. For reviews, see: (a) S. Oae and T. Numata, "The Pummerer Type of Reactions," in "Isotopes in Organic Chemistry", vol. 5, ed. by E. Buncel and C. C. Lee, Elsevier 1980, chapter 2, 45.
2. (b) S. Oae, T. Numata, and T. Yoshimura, "Heterosulphonium Salts," in "The Chemistry of the Sulphonium Group" ed. by S. Patai and C. J. M. Stirling, John Wiley & Sons 1981, part 2, Chapter 15, 571.
3. (c) O. D. Lucchi, U. Miotti, and G. Modena, Organic Reactions, 1991,40, 157.
4. S. Iriuchijima, K. Maniwa, and G. Tsuchihashi, J. Am. Chem. Soc. 1974, 96, 4280.
5. H. Sugihara, R. Tanikaga, and A. Kaji, Synthesis 1978, 881.
6. T. Sakamoto, K. Tanji, S. Niitsuma, T. Ono, and H. Yamanaka, Chem. Pharm. Bull. 1980, 28, 3362.
7. Y. Kita and N. Shibata, Synlett 1996, 289.
8. 2S: C, 68.27; H, 5.73. Found: C, 68.24; H, 5.73.
9. I. D. Kersey, C. W. G. Fishwick, J. B. C. Findlay, and P. Ward, Tetrahedron, 1995, 51, 6819. (Figure Presented)
10. +) (matrix: 2-nitrophenyl octyl ether).
11. 11 All non-hydrogen atoms were refined anisotropically. The final cyclic of full-matrix least-squares refinement was based on 2224 observed reflections (I > 3.00σ(I)) and 229 variable parameters.
12. SIR92 : A. Altomare, M. C. Burla, M. Camalli, M. Cascarano, C. Giacovazzo, A. Guagliardi, G. Polidori, 1994.
13. DIRDIF94 : P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, R. de Gelder, R. Israel, and J. M. M. Smits, 1994.