REACTION OF beta-TRIFLUOROACETYLKETENE ACETALS AND beta-TRIFLUOROACETYLVINYL ETHERS WITH 1,2-PHENYLENEDIAMINES ACCESSING FLUORINE-CONTAINING BENZO[b][1,4]DIAZEPINE DERIVATIVES: A MOLECULAR ORBITAL CALCULATION STUDY

[摘要]：beta-Trifluoroacetylketene acetals (1) were found to react easily with 1,2-phenylenediamines to give dihydrobenzodiazepinols (5a) together with benzodiazepines (6a) under very mild conditions. In contrast, beta-trifluoroacetyl-alpha-phenylvinyl ethers (2) and beta-trifluoroacetylvinyl ethers (3) exclusively yielded O-N exchanged products (9) when they were reacted with 1,2-phertylenediamines. The factors determining product formation by the reaction of each of three similar substrates (1-3) with 1,2-phenylenediamine were elucidated on the basis of molecular orbital calculations. The dehydration processes converting dihydrobenzodiazepinols (5 and 7) to the corresponding benzodiazepines (6 and 8) are also discussed.

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