Formation of Dichloromethyl Phenyl Ethers as Major Products in Photo-Reimer-Tiemann Reaction without Base

Article abstract of DOI:10.1016/0040-4020(95)00235-Z

Photolysis of phenols 1a-d in chloroform or carbon tetrachloride afforded the corresponding di- or trichloromethyl phenyl ethers (2a-d or 6a-d, respectively).In chloroform, hydroxybenzaldehydes 4a-d or 5 and phenyl formates 3a-d were obtained as minor photoproducts.In carbon tetrachloride, traces of salicyloyl chloride (7), phenyl salicylate (8) and phenyl p-hydroxybenzoate (9) were detected starting from the parent phenol (1a).The obtained results agree with the involvement of an electron transfer mechanism.