The reaction of tetracoordinated thiophosphoryl compounds with p-aminophenol

Abstract

The reaction of RP(S)Cl2 (R = PhO, EtO, Me2CHO, Et2N, MeS, Cl) with o-aminophenol in the presence of triethylamine involved the cleavage of phosphorus-sulfur double bond and the displacement of some P-R bonds to give a pentacoordinated phosphorus compound I. The cyclic thiophosphonates II (Z = NH, O) reacted with o-aminophenol to yield spirophosphoranes III, resp. The cyclic thiophophates IV (Z1, R1 = NH, Me2CHO; O, PhO) which contain phenoxy and alkoxy groups underwent exchange reaction between o-iminophenoxy and o-phenylenedioxy groups in addition to the cleavage of phosphorus-sulfur double bond and the displacement of phenoxy and alkoxy groups. The mechanism of these reactions were discussed with respect to the electronegativity of phosphorus, the activity of hydrogen and the stability of P-R bond.

Key words: REACTION MECHANISM, ORGANO PHOSPHORUS COMPOUNDS, ACYL CHLORIDES, PHOSPHOROTHIOIC ACID P, AMINOPHENOL, HYDROGEN SULFIDE, PHOSPHOROUS HETEROCYCLIC COMPOUNDS, TRIETHYL AMINE, PENTACOORDINATE, TETRACOORDINATE

CLC Number:

O627

Cite this article

LIU LUNZU;CAI BAOZHONG;CHEN RUYU. The reaction of tetracoordinated thiophosphoryl compounds with p-aminophenol[J]. Acta Chimica Sinica, 1987, 45(11): 1096-1100.

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