Mechanisms of nucleophilic attack at carbon-nitrogen double bonds. The reaction of aryl N-arylbenzimidates with methoxide ion
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Rate data for the reaction of three series of aryl N-arylbenzimidates with methoxide ion at 303 K are presented. Linear Hammett plots were obtained for each series. Solvent isotope effects have also been measured. The results are interpreted in terms of rate-determining formation of a tetrahedral intermediate, irrespective of the nature of the substituent.
1968 ◽
Vol 46
(18)
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pp. 2887-2894
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1971 ◽
pp. 2282
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1982 ◽
Vol 78
(4)
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pp. 1103
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1985 ◽
Vol 260
(29)
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pp. 15561-15565
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1984 ◽
Vol 80
(8)
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pp. 2287
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