MMPP (Magnesium Monoperoxyphthalate) in acetonitrile; a new approach to the synthesis of lactones via Baeyer-Villiger oxidation of cyclic ketones

Synthetic Communications

Volumn 26, Issue 24, 1996, Pages 4591-4596

  Hirano, Masao ^a   Yakabe, Shigetaka ^a   Satoh, Akiko ^a   Clark, James H ^b   Morimoto, Takashi ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0030473567     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608004783     Document Type: Article

References (13)

1. Hignett, G. J. European Patent Appl., 27693 (1981).
2. MMPP is commercially available from Tokyo Chemical Industry Co., Ltd., Aldrich Chemical Co., Ltd., and Interox Chemicals Ltd.
3. (a) Kariuki, B. M. and Jones, W. Mol. Cryst. Liq. Cryst., 186, 45 (1990):
4. (b) Griffith, W. P., Skapski, A. C. and West, A. P. Inorg. Chim. Acta, 65, L249 (1982).
5. Brougham, P., Cooper, M. S., Cummerson, D. A., Heaney, H. and Thompson, N. Synthesis, 1987, 1015.
6. A concise review of MMPP chemistry is available; Heaney, H. Aldrichimica Acta, 26, 35 (1993).
7. For comprehensive reviews concerning Baeyer-Villiger oxidations, see: Hassal, C. H. Org. React., 9, 73 (1957); Krow, G. R. ibid., 43, 251 (1993).
8. For comprehensive reviews concerning Baeyer-Villiger oxidations, see: Hassal, C. H. Org. React., 9, 73 (1957); Krow, G. R. ibid., 43, 251 (1993).
9. It appears expedient to add MMPP in portions as described in Method B in cases where a large amount of the reagent is employed. If this is not done, formation of a solid crust on the wall of the reaction vessel is sometimes observed, which leads not only to a decrease in conversion of the ketone and the yield of the lactone, but also to poor reproducibility of the reaction.
10. Brown, H. C., Garg, C. P. and Liu, K. -T. J. Org. Chem., 36, 387 (1971).
11. Mozingo, R. Org. Synth., Coll. Vol. III, p. 181 (1955).
12. Miyashita, M., Hara, S. and Yoshikoshi, A. J. Org. Chem., 52, 2602 (1987).
13. Kharasch, M. S. and Sosnovsky, G. J. Org. Chem., 23, 1322 (1958).