Solvolysis of 2-thioxo bridgehead compounds as compared with their 2-oxo homologs: Evidence for marked π-conjugation in 2-thioxo carbocation

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2241-2244

  Tokunaga, Kazuhiko ^a   Ohga, Yasushi ^a   Takeuchi, Ken'ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[2.2.2]OCTANE DERIVATIVE; BICYCLO[3.2.2]NONANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SOLUBILITY; STRUCTURE ACTIVITY RELATION;

EID: 0030007335     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00265-1     Document Type: Article

References (19)

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13. Okazaki, R.; Inoue, K.; Inamoto, N. Bull. Chem. Soc. Jpn. 1981, 54, 3541-3545.
14. 3; q, J = 277.2 Hz), 262.3 (C).
15. Takeuchi, K.; Ikai, K.; Shibata, T.; Tsugeno, A. J. Org. Chem. 1988, 53, 2852-2855.
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17. 13C NMR for the crude product.
18. 2), 106.0 (C).
19. We assume that the direct formation of 17 through "frontside SN2" of 6a-OTr would be highly improbable. The α-carbonyl thiol 15 is assumed to have been formed during work-up.