Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
The Reaction of o-Phenylenediamine with Phenyl Phosphorodichloridate. Synthesis and Reactions of 2-Phenoxy-1, 3-dihydro-2H-1, 3, 2-benzodiazaphosphole-2-oxide and Related Compounds
TORU KOIZUMIYOSHIYUKI ARAIEIICHI YOSHII
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1973 年 21 巻 1 号 p. 202-206

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The reaction of o-phenylenediamine with phenylphosphorodichloridate was reexamined. Unlike Autenrieth and Bolli's report, 2-phenoxy-1, 3-dihydro-2H-1, 3, 2-benzodiazaphosphole 2-oxide (I) has not been obtained by their procedure. Instead, phenyl hydrogen N-(2-aminophenyl) phosphoroamidate (V) was obtained by the reaction in refluxing benzene. When the reaction was carried out by the fusion method, a roughly equal amount of V and o-phenylenediamine salt of diphenyl phosphate (VI) were isolated. The solubility and reactivity of both compounds V and VI were compared with those of the Autenrieth and Bolli's compound and it was concluded that their synthesis should be refuted. Finally the diazaphosphole I was synthesized by the reaction in bromobenzene and the properties of I was quite different from those of the Auterieth and Bolli's compound.
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© The Pharmaceutical Society of Japan
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