Oxirane, 2-benzoyl-3-

When the unsaturated Y-benzoyl a-amino ester 443 was treated with MCPBA, the oxirane 444 formed first immediately underwent an intramolecular rearrangement with cleavage of the oxirane ring by attack of the amide oxygen to give a 3 1 mixture of two cis- and /ra r-isomers of 5,6-dihydro-47/-l,3-oxazine derivatives 445 and 446, the configurations of which were determined via their 0-3,5-dinitrobenzoyl derivatives (Scheme 85) <2003M69>. 

Benzoyl Di-O-benzoyl-3-fluoro-ElOa. 578 (0-S02-NR2 -+ F) Methyl 5-0-Benzyl-2-fluoro-ElOb, 145 (Oxirane + KHF,)... 

By the alkylation of N-benzoyl uracil with the chiral 2-trityloxy-oxirane was obtained glycoside-like derivative N-[l-(2-hydroxy-3-trityloxy-propyl)-2-oxo-l,2-dihydroxypyrimidin-4-yl]-N-methylbenzamide as a single isomer. From N-[1-(2-hydroxy-3-trityloxy-propyl)-2-oxo-l,2-dihydroxypyrimidin-4-yl]-N-methylbenzamide and toluene-(4-sulfomethyl)phosphonic acid diethyl ester was prepared [2-[(benzoylmethylamino)-2-oxo-2H-pyrimidin-l-yl]-l-trityloxymethylethoxymethyljphosphonic acid diethyl ester. As a result of... 

S,4S)-4-Benzoyl-3-[(/ )-l-hydroxy-ethyl]-2-oxo- E16b, 189 (aus Aminocarbonyl-oxiran)... 

Similarly, methyl-2,2,3-trimethyl-l-phenylcyclopropane-l-carboxylate (two isomers) was obtained from lb in a solution of 2-methylbut-2-ene. Oxirane la was synthesized from benzoyl... 

Demgegeniiber ergibt die Photolyse von 3,3-Dimethyl- (la R=CH3) oder von 3-Methyl-3-phenyl-2-benzoyl-oxiran (lb R=CSHS) 3-Hydroxy-4-oxo-2-viethyl-4-phe-nyl-buten-(l) (Ila 25% d.Th.) bzw. 3-Hydroxy-4-oxo-2,4-diphenyl-buten-(l) (lib 64% d.Th.)1- ... 

Die Photoisomerisierung von 3-PhenyI-2-benzoyl-oxiran fiihrt zu ],3-Dioxo- 1,3-diphenyl- propan (25% d.Th.)2- . Analoge Ergebnisse lassen sich miteinem 4-Chlor-benzoyl-oder 3-Nitro-benzoyl-Rest erzielen2-3. 

Aromatic halo ketones can also be condensed with aromatic aldehydes for example, eo-bromoacetophenone and p-nitrobenzaldehyde afford 2-benzoyl-3-(p-nitrophenyl)oxirane in 88% yield 139... 

Reaction with benzoyl chloride. Benzoyl chloride reacts with dichloro-methylUthium to give the oxirane (1) or the carbinol (2), depending on the reaction conditions. ... 

The reaction of spiro[indole-3,2 -oxiranes] (174) with thioacetamide in the presence of LiBr as a catalyst in an aqueous medium produced substituted 2 -amino-4 -benzoyl-2-methylspiro[indole-3,5 -[l,3]oxathiolane]-2(lH)-ones (175). The reaction was carried out under both microwaves and sonication, and the results were also compared with the conventional method (Dandia et al. 2010). In general, improvement in rate and yields were observed when reaction was carried out under sonication as compared to microwave irradiation and the conventional method (Scheme 8.56). 

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