The snythesis of phenlglycine utilizing some photoreactions is attempted.
Phenylacetic acid is chlorinated photochemically in carbon disulfide and carbon tetrachloride solvents. α-chlorophenylacetic acid is separated from the chlorination product mixtures and identified by infrared and nmr spectra. The amination of α-chlorophenylacetic acid yielded the desired dl-phenylglycine. Phenylglycine is identified by infrared spectrum and this layer chromatogram. The spectrum and chromatogram were exactly same as those of authentic sample. The overall yield was about 16% in carbon disulfide solvent, and about 4% in carbon tetrachloride. Benzene was tested as solvent but significant side reactions were observed and the separation of the reaction products was complicated.
Sensitized photophenylation of easily available glycine is also attempted utilizing benzoylperoxide as a phenyl radical source in benzene or acetone solvent.
광반응을 이용한 phenylglycine 의 합성이 시도되었다.
이 황화탄소와 사염화탄소용매에서 광화학적으로 plenylacetic acid 에 염소화반응을 일으켰다. 염소화반응 혼합물로부터 α -chlorophenylacetic 를 분리하여 I.R. 과 N.M.R. 스펙트럼으로 확인하였다. α-chlorophenylacetic acid 를 amination 시켜 dl-phenylglycine 을 합성하였고 합성된 phenylglycine 은 I.R. 과 T.L.C 로 확인하였다.
이황화탄소용매에서는 16%, 사염화탄소용매에서는 4%의 수득률을 각각 얻었다. 벤젠을 용매로 하였을 때는 부반응이 크게 일어났고 반응혼합물의 분리가 용이하지 않았다. 또한 쉽게 구할수 있는 glycine 의 증감제를 사용한 광페닐화반응 (photophenylation)이 benzoylperoxide 를 페닐라디칼 자원 (phenyl radical source)으로 삼아 벤젠과 아세톤 용매에서 시도 되었다.
