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Paper | Special issue | Vol 77, No. 1, 2009, pp.461-469
Published online, 1st September, 2008
DOI: 10.3987/COM-08-S(F)43
Reaction of β,β-Bis(trifluoroacetyl)vinyl Esters and β-Trifluoroacetylvinyl Esters with 1,2-Phenylenediamines Accessing Fluorine-containing Benzo[b][1,4]diazepine Derivatives — A Study about the Reaction Based on Molecular Orbital Calculations

Norio Ota, Yasuhiro Kamitori,* Takehisa Tomoda, Naoya Terai, and Etsuji Okada*

*Department of Chemical Science and Engineering, Faculty of Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan


β,β-Bis(trifluoroacetyl)vinyl ether (1) reacted with 1,2-phenylenediamine to give dihydrobenzodiazepinol (4a) selectively, whereas β-trifluoroacetylvinyl ether (2) and β-trifluoroacetyl-α-phenylvinyl ether (3) 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.