STEREOSELECTIVITY IN FRAGMENTATION AND REARRANGEMENT OF ALPHA-HYDROXYIMINOPHOSPHINATES AND HYDROXYIMINOPHOSPHONATES - A SYNTHETIC APPROACH TO ACYLPHOSPHONAMIDATES AND PHOSPHORAMIDATES - CRYSTAL-STRUCTURES OF METHYL (E)-ALPHA-HYDROXYIMINOBENZYLPHENYLPHOSPHINATE AND METHYL BENZOYLPHENYLPHOSPHONAMIDATE

被引：21

作者：

BREUER, E ^{[1
]}

SCHLOSSMAN, A ^{[1
]}

SAFADI, M ^{[1
]}

GIBSON, D ^{[1
]}

CHOREV, M ^{[1
]}

LEADER, H ^{[1
]}

机构：

[1] ISRAEL INST BIOL RES,IL-70450 NESS ZIONA,ISRAEL

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 12期

关键词：

D O I：

10.1039/p19900003263

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of methyl benzoylphenylphosphinate 1 with hydroxylamine gave methyl alpha-hydroxyiminobenzylphenylphosphinate 2 as a mixture of E and Z isomers with the E isomer predominating. Pure (E)-2 when heated gave methyl N-benzoylphenylphosphonamidate 3 as the sole product. In contrast, (Z)-2 when heated gave, as a result of fragmentation, mainly methyl hydrogen phenylphosphonate 4 and benzonitrile, together with methyl N-phenylcarbamoylphenylphosphinate 5 as the minor product; the latter results from Beckmann rearrangement of (Z)-2. Analogous behaviour is exhibited by the two geometrical isomers of dimethyl alpha-hydroxyiminobenzylphosphonate 8. The crystal structures of methyl (E)-alpha-hydroxyiminobenzylphenylphosphinate (E)-2 and methyl benzoylphenylphosphonamidate 3 are reported.

引用

页码：3263 / 3269

页数：7