Mercuric nitrate-mediated deprotection of oximes, hydrazones, and semicarbazones

Synthetic Communications

Volumn 34, Issue 12, 2004, Pages 2289-2294

  De, Surya Kanta ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

Hydrazones; Mercuric nitrate; Oximes; Semicarbazones

Indexed keywords

CARBONYL DERIVATIVE; HYDRAZONE DERIVATIVE; MERCURIC NITRATE; OXIME; REAGENT; SEMICARBAZONE DERIVATIVE; SILICA GEL;

ARTICLE; CHEMICAL STRUCTURE; DEPROTECTION REACTION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME;

EID: 3142677797     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120038512     Document Type: Article

References (21)

1. Cheronis, N.D.; Entrikin, J.B. Identification of Organic Compounds; Interscience: New York, 1963; 318-320.
2. Barton, D.H.R.; Beaton, J.M.; Gelker, L.E.; Pechet, M.M. A new photochemical reaction. J. Am. Chem. Soc. 1961, 83, 4076-4083.
3. Greene, T.W.; Wuts, P.G. Protective Groups in Organic Synthesis, 3rd Ed.; Wiley: New York, 1999; 352-358.
4. Whitesell, J.K.; Whitesell, M.K. Alkylation of ketones and aldehydes via their nitrogen derivatives. Synthesis 1983, 517-536.
5. Maloney, J.R.; Lyle, R.E.; Saavedra, J.E.; Lyle, G.G. Oxidative deoximation with pyridinium chlorochromate. Synthesis 1978, 212-213.
6. Drabowicz, J. Rapid deoximation with pyridinium chlorochromate/hydrogen peroxide system. Synthesis 1980, 125-126.
7. Rao, C.G.; Radhakrishna, A.S.; Singh, B.B.; Bhatnagar, S.P. Oxidative cleavage of oximes with triethylammonium chlorochromate. Synthesis 1983, 808.
8. Azipura, J.M.; Juaristi, M.; Lecea, B.; Palomo, C. Reagents and synthetic methods-40: halosilanes/chromium trioxide as efficient oxidizing reagents. Tetrahedron 1985, 41, 2903-2911.
9. Shim, S.B.; Kim, K.; Kim, Y.H. Direct conversion of oximes with dinitrogen tetroxide. Tetrahedron Lett. 1987, 28, 645-648.
10. 2 over TS-1. Tetrahedron Lett. 1994, 35, 5493-5496.
11. Bangar, B.P.; Kunde, L.; Thote, J.L. Deoximation with N-haloamides. Synth. Commun. 1997, 27, 1149-1152.
12. Ayhan, H.D.; Tanyeli, E.A.; Altinel, E. Manganese triacetate mediated regeneration of carbonyl compounds from oximes. Tetrahedron Lett. 1997, 38, 7267-7270.
13. Bose, D.S.; Narraiah, A.V. A facile method for the conversion of oximes and tosylhydrazones to carbonyl compounds with Dess-Martin periodane. Synth. Commun. 1999, 29, 937-941.
14. Chen, F.; Liu, A.; Yan, Q.; Liu, M.; Zhang, D.; Shao, L. Tetrabutylammonium peroxydisulfate in organic synthesis-IV. An efficient, highly selective oxidative deoximation by tetrabutylammonium peroxydisulfate. Synth. Commun. 1999, 29, 1049-1056.
15. Heravi, M.M.; Beheshtiha, Y.S.; Ghassemzadeh, M.; Hekmatshoar, R.; Sarmad, N. Solid state deoximation with clay supported ammonium chlorochromate: regeneration of carbonyl compounds using microwave in a solventless system. Monatsh Chem. 2000, 131, 187-190.
16. Heravi, M.M.; Ajami, D.; Mojtahedi, M.M. Regeneration of carbonyl compounds from oximes on clayfen under conventional heating and microwave irradiation. J. Chem. Res. 2000, 126-127.
17. (a) Varma, R.S.; Dahiya, R.; Saini, R.K. Solid state regeneration of ketones from oximes on a wet silica supported sodium periodate using microwaves. Tetrahedron Lett. 1997, 38, 8819-8820;
18. (b) Boruah, A.; Boruah, B.; Prajapati, D.; Sandhu, J.S. Regeneration of carbonyl compounds from oximes under microwave irradiation. Tetrahedron Lett. 1997, 38, 4267-4268.
19. 6: as a versatile and efficient reagent for cleavage of carbon-nitrogen double bonds under heterogeneous and non-aqueous conditions. Synth. Commun. 2001, 31, 3775.
20. 2. Synth. Commun. 2002, 32, 315-318.
21. Nishiguchi, T.; Asano, F. Oxidation of alcohols by metal nitrates supported on silica gel. Tetrahedron Lett. 1988, 29, 6265-6266.