Phthalimidesulfenyl chloride 12: Generation and trapping of para- monothioquinones

Synthesis

Volumn , Issue 6, 1999, Pages 1046-1050

  Cantini, Beatrice ^a   Capozzi, Giuseppe ^a   Menichetti, Stefano ^a   Nativi, Cristina ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Desulfurization; Hetero Diels Alder reaction; p thioquinones; Phthalimidesulfenyl chloride; Spiro dihydrothiopyrans

Indexed keywords

PHTHALIMIDE DERIVATIVE; QUINONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033034591     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3504     Document Type: Article

References (19)

1. Capozzi, G.; Falciani, C.; Menichetti, S.; Nativi, C., J. Org. Chem. 1997, 62, 2611.
2. Bock, H.; Mohmand, S.; Hirabayashi, T.; Maier, G.; Reisenauer, H. P., Chem. Ber. 1983, 116, 273.
3. Lakshmikantham, M. V.; Raasch, M. S.; Cava, M. P.; Bott, S. G.; Atwood, J. L., J. Org. Chem. 1987, 52, 1874.
4. Raasch, M. S., J. Org. Chem. 1979, 44, 632.
5. Lakshmikantham, M. V.; Levinson, M.; Menachery, M.; Cava, M. P., J. Org. Chem. 1986, 51, 411.
6. Huang, N-Z.; Lakshmikantham, M. V.; Cava, M. P., J. Org. Chem. 1987, 52, 169.
7. Capozzi, G.; Menichetti, S.; Nativi, C.; Rosi, A.; Valle, G., Tetrahedron 1992, 48, 9023.
8. Capozzi, G.; Corti, A.; Menichetti, S.; Nativi C., Tetrahedron Lett. 1997, 38, 5041.
9. a) Capozzi, G.; Menichetti, S.; Nativi, C.; Rosi, A.; Franck, R. W., Tetrahedron Lett. 1993, 34, 4253.
10. b) Capozzi, G.; Franck, R. W. G.; Mattioli, M.; Menichetti, S.; Nativi, C.; Valle, G. J. Org., Chem. 1995, 60, 6416.
11. Capozzi, G.; Menichetti, S.; Nativi, C.; Vergamini, C., Synthesis 1998, 915.
12. Capozzi, G.; Menichetti, S.; Nativi, C.; Simonti, M-C., Tetrahedron Lett. 1994, 35, 9451.
13. Capozzi, G.; Falciani, C.; Menichetti, S.; Nativi, C., Gazz. Chim. It. 1996, 126, 227.
14. a) Tamaru, Y.; Satomi, H.; Kitao, O.; Yoshida, Z., Tetrahedron Lett. 1984, 25, 2561.
15. b) Ohno, A.; Ohnishi, Y.; Tsuchihashi, G., Tetrahedron 1968, 25, 871.
16. Compounds 25 and 26 can be considered as the products of a para-Claisen rearrangement. See for example: a) Hurd, C. D.; Pollack, M. A., J. Org. Chem. 1938, 3, 550.
17. b) Alexander, E. R.; Kluiber, R. W., J. Am. Chem. Soc. 1951, 73, 4304.
18. Scheinmann, F.; Barner, R.; Schmid, H., Helv. Chim. Acta 1968, 51, 1603.
19. Commercial CW2 Raney Nickel was activated following the literature procedure: Vogel, A. Practical Organic Synthesis; Longman: Birmingham, AL, 1962, p 870.