Formation of a cyclic tetrahedral intermediate by the addition of water to 2-methyl-4H-3,1-benzoxazine followed by ring opening to 2-aminobenzyl acetate and 2-acetylaminobenzyl alcohol; pH-dependence of rate of reaction and product ratio

Canadian Journal of Chemistry

Volumn 77, Issue 5-6, 1999, Pages 1035-1041

  Dixon, Wendy J ^a   Hibbert, Frank ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

Addition; Hydrolysis; Mechanism; pH profile; Tetrahedral intermediate

Indexed keywords

BASE; BENZOXAZINE DERIVATIVE; BENZYL ACETATE; BENZYL ALCOHOL DERIVATIVE; BUFFER; HYDROXIDE; WATER;

ARTICLE; CHEMICAL REACTION KINETICS; HYDROLYSIS; PH; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

ADDITION REACTIONS; REACTION INTERMEDIATES;

ADDITION; BENZOXAZINE; HYDROXIDE IONS; PH DEPENDENCE; PH PROFILE; PH-DEPENDENCE; PROTONATED; RATE OF REACTION; RING OPENING; TETRAHEDRAL INTERMEDIATES;

PROTONATION;

EID: 0033306224     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v99-091     Document Type: Article

References (6)

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3. A.C. Satterthwait and W.P. Jencks. J. Am. Chem. Soc. 96, 7031 (1974).
4. D.D. Perrin. In Dissociation constants of inorganic acids and bases in aqueous solution. 2nd ed. Butterworths, London. Pergamon Press, London. 1982.
5. D.D. Perrin. In Dissociation constants of organic bases in aqueous solution. Butterworths, London; Pergamon Press, Oxford. (1st ed.) 1965; (supplement) 1972.
6. W.J. Dixon and F. Hibbert. J. Chem. Soc. Perkin Trans. 2, 795 (1994).