Oxepins reduction reaction

Arene Oxides-Oxepins 4. Oxidation-Reduction Reactions... 

Oxepin, 2-acetoxy-2,3,4,5-tetrahydro-thermal reactions, 7, 559 Oxepin, 3-chloro-synthesis, 3, 725 Oxepin, 2,3-dihydro-cycloaddition reactions, 7, 563 nucleophilic reactions, 7, 562 reduction, 7, 563 Oxepin, 2,5-dihydro-synthesis, 7, 578, 580 Oxepin, 4,5-dihydro-formation, 7, 579 reduction, 7, 563 synthesis, 7, 579 Oxepin, 2,7-dimethyl-NMR, 7, 552... 

Oxepin, 4-ethoxycarbonyl-2,3,6,7-tetrahydro-synthesis, 7, 578 Oxepin, 2-methyl-enthalpy of isomerization, 7, 555 Oxepin, 2,3,4,5-tetrahydro-reduction, 7, 563 synthesis, 7, 578 Oxepin, 2,3,4,7-tetrahydro-synthesis, 7, 578 Oxepin, 2,3,6,7-tetrahydro-oxidation, 7, 563 reduction, 7, 563 Oxepin-2,6-dicarboxylic acid stability, 7, 565 Oxepinium ions synthesis, 7, 559 Oxepins, 7, 547-592 antiaromaticity, 4, 535 applications, 7, 590-591 aromatization, 7, 566 bond lengths and angles, 7, 550, 551 cycloaddition reactions, 7, 27, 569 deoxygenation, 7, 570 dipole moment, 7, 553 disubstituted synthesis, 7, 584... 

Arene oxides show the characteristic reactions of epoxides (isomerization to ketones, reductions to alcohols, nucleophilic additions, deoxygenations) and olefins or conjugated dienes (catalytic hydrogenation, photochemical isomerization, cycloaddition, epoxidation, metal complexation). Where a spontaneous, rapid equilibration between the arene oxide and oxepin forms exists, reactivity typical of a conjugated triene is also found. 

Reactions of Fused Azepines. The morphanthridene derivative (40) undergoes an interesting rearrangement to (42) when treated with primary amines the reaction involves a transamidation which converts (41) into (42). Reversal, with concurrent reduction of the carbonyl, is induced by lithium aluminium hydride. The diarylethylene-type double-bond in some dibenz-azepines and -oxepines can be reduced conveniently and in high yield, using magnesium in methanol. 

Reaction of 3-benzoylcyclopropene 138 with 1-hexyne in the presence of [RhCl(CO)2l2 afforded oxepin 139 (62%) and phenol 140 (8%) (Scheme 2.93) [148]. Treatment of oxepin 139 with HCl induced rearrangement to phenol 140. The reaction is believed to proceed via (i) formation of (vinylcarbene)rhodium (ii) [2+2] cycloaddition with alkyne (iii) rearrangement to eight-membered oxarhodacycle and (iv) reductive elimination. 

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