O Phenylene carbonate

Concentration of the filtrate yields a second crop of impure product, which is recrystallized from toluene and then melts at 119-120°. The combined yield of pure white o-phenylene carbonate from the first and second crops is 107-116 g. (79-86%). 

Oxygen. The very weak aromaticity in vinylene carbonate (92) and o-phenylene carbonate is enhanced by protonation to 93 and 97, respectively, as evidenced by electronic spectra of 94135 and lH NMR spectra of 93136 (Scheme 44). 

The protonation of o-phenylene carbonate [195], a further analogue of coumarin in which a C=C group has been replaced by O,... 

The phosgenation of catechol is of high interest, because the resulting o-phenylene carbonate is the key starting material for the preparation of the insecticide Propoxur as shown in schenne 168. 

With heterogeneous Pd/C catalyst, CU2O showed superior performance in oxidative carbonylation of phenols [29]. However, copper ICCs promote side reactions such as phenol oxidation by oxygen to form 2,2-biphenol [16] or formation of o-phenylene carbonate [51]. 

A final example of aryne formation involves the reaction of o-phenylene carbonate (90) with phosphines. An analogous reaction with thiocarbonates (91) fails as does generation of the anion of 2-phenyl-1,3-benzodioxole (92), which had been expected to lose benzoate ion to give benzyne. ... 

Phosgenation of catechol affords o-phenylene carbonate, which is the key starting... 

The smallest possible five-membered aromatic cyclic carbonate is a derivative of catechol benzo-l,3-dioxolan-2-one (o-phenylene carbonate) (1, Scheme 13). It was synthesized using three different methods the reaction of catechol with phosgene (or its dimer or trimer), ° the reaction of catechol with chloroformate, ° or by transesterification of catechol with diphenyl carbonate. ... 

---