REACTION OF beta,beta-BIS(TRIFLUOROACETYL)VINYL ETHERS AND beta-TRlFLUORO ACETYL VINYL ETHERS WITH 1,2-PHENYLENE-DIAMINES ACCESSING FLUORINE-CONTAINING BENZO[b][1,4]-DIAZEPINE DERIVATIVES-A STUDY ABOUT THE REACTION BASED ON MOLECULAR ORBITAL CALCULAT

摘要

beta,beta-Bis(trifluoroacetyl)vinyl ether(1)reacted with 1,2-phenylenediamine to give dihydrobenzodiazepinol(4a)selectively,whereas beta-trifluoroacetylvinyl ether (2)and beta-trifluoroacetyl-alpha-phenylvinyl ether beta)gave the corresponding O-N exchange products(6b,c)when reacted with 1,2-phenylenediamine.The factors determining the reaction products of the reaction of three substrates 1-3 having similar structures with 1,2-phenylenediamine were elucidated on the basis of molecular orbital calculations.The dehydration processes from dihydrobenzodiazepinols(4 and 8)to benzodiazepines(5 and 7)are also discussed.