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Volumn 64, Issue 17, 1999, Pages 6522-6526

Preparation of novel haloazide equivalents by iodine(III)-promoted oxidation of halide anions

Author keywords

[No Author keywords available]

Indexed keywords

ANION; AZIDE; HALIDE; IODINE;

EID: 0033588364     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990478p     Document Type: Article
Times cited : (72)

References (30)
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    • For the construction of tetrazoles via the "Hassner-Ritter" reaction see: (a) Ranganathan, S.; Ranganathan, D.; Mehrotra, A. K. Tetrahedron Lett. 1973, 14, 2265-2268. (b) Moorthy, S. N.; Devaprabhakara, D. Tetrahedron Lett. 1975, 16, 257-260.
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    • For recent studies on dialkyl and diphenyl halogen-ate complexes refer to: (a) Schulze, V.; Brönstrup, M.; Böhm, V. P. W.; Schwerdtfeger, P.; Schimeczek, M.; Hoffmann, R. W. Angew. Chem. 1998, 110, 869-871; Angew. Chem., Int. Ed. Engl. 1998, 37, 824-826. (b) Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1991, 113, 1414-1416 and references therein.
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    • For recent studies on dialkyl and diphenyl halogen-ate complexes refer to: (a) Schulze, V.; Brönstrup, M.; Böhm, V. P. W.; Schwerdtfeger, P.; Schimeczek, M.; Hoffmann, R. W. Angew. Chem. 1998, 110, 869-871; Angew. Chem., Int. Ed. Engl. 1998, 37, 824-826. (b) Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1991, 113, 1414-1416 and references therein.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 824-826
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    • For recent studies on dialkyl and diphenyl halogen-ate complexes refer to: (a) Schulze, V.; Brönstrup, M.; Böhm, V. P. W.; Schwerdtfeger, P.; Schimeczek, M.; Hoffmann, R. W. Angew. Chem. 1998, 110, 869-871; Angew. Chem., Int. Ed. Engl. 1998, 37, 824-826. (b) Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1991, 113, 1414-1416 and references therein.
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    • Compound 5 can only be generated in situ; its precise structure is unknown: (a) Kirschning, A.; Domann, S.; Dräger, G.; Rose, L. Synlett 1995, 767. (b) Magnus, P.; Lacour, J. J. Am. Chem. Soc. 1992, 114, 767. (c) Magnus, P.; Lacour, J.; Evans, P. A.; Roe, M. B.; Hulme, C. J. Am. Chem. Soc. 1996, 118, 3406 and references therein.
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    • and references therein
    • Compound 5 can only be generated in situ; its precise structure is unknown: (a) Kirschning, A.; Domann, S.; Dräger, G.; Rose, L. Synlett 1995, 767. (b) Magnus, P.; Lacour, J. J. Am. Chem. Soc. 1992, 114, 767. (c) Magnus, P.; Lacour, J.; Evans, P. A.; Roe, M. B.; Hulme, C. J. Am. Chem. Soc. 1996, 118, 3406 and references therein.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3406
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    • note
    • 3.
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    • In their study of the reaction of glycal 9 and iodoazide, generated by Hammer's procedure (ref 11), Lafont and Descotes observed pronounced α-selectivity: (a) Lafont, D.; Descotes, G. Carbohydr. Res. 1987, 166, 195-209. (b) Lafont, D.; Guilloux, P.; Descotes, G. Carbohydr. Res. 1988, 193, 61-73.
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    • Lafont, D.1    Descotes, G.2
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    • In their study of the reaction of glycal 9 and iodoazide, generated by Hammer's procedure (ref 11), Lafont and Descotes observed pronounced α-selectivity: (a) Lafont, D.; Descotes, G. Carbohydr. Res. 1987, 166, 195-209. (b) Lafont, D.; Guilloux, P.; Descotes, G. Carbohydr. Res. 1988, 193, 61-73.
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