Organotin-mediated monoacylation of diols with reversed chemoselectivity. Mechanism and selectivity

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5257-5263

  Roelens, Stefano ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000522903     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960453f     Document Type: Article

References (24)

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9. For recent alternative methods, see: Bailey, W. F.; Zarcone, L. M. J.; Rivera, A. D. J. Org. Chem. 1995, 60, 2532 and references cited therein.
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12. Mandolini, L. In Advances in Physical Organic Chemistry; Academic Press: London, 1986; Vol. 22, p 1.
13. Roelens, S. J. Chem. Soc., Perkin Trans 2 1988, 1617.
14. 2-benzoyl > p-MeO-benzoyl).
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20. Although tetrahedral intermediates have been established for intramolecular reactions of substituted ethylene glycols (see, for example: (a) Santry, L. J.; Azer, S.; McClelland, R. A. J. Am. Chem. Soc. 1988, 110, 2909. (b) McClelland, R. A.; Seaman, N. E.; Cramm, D. J. Am. Chem. Soc. 1984, 106, 4511), the present data do not allow the assessment of this species as a real intermediate or a transition state.
21. (a) Roelens, S.; Taddei, M. J. Chem. Soc., Perkin Trans 2 1985, 799.
22. (b) Luchinat, C.; Roelens, S.. J. Am. Chem. Soc. 1986, 108, 4873.
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