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Reaction of di- and trialkyl phosphites with isatins

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
22
Issue
2
Identifiers
DOI: 10.1016/0040-4020(66)80002-9

Abstract

Abstract Isatins (Ia–c) react with dialkyl phosphites to produce the corresponding dioxindole-3-phosphonic esters (IIa–i). 4:5-Benzocoumaran-2, 3-dione (III), the oxygen analogue of 4:5-benzoisatin reacts similarly with diethyl phosphite giving the α-hydroxyphosphonate (IV). Trialkyl phosphites effect the conversion of the isatins (Ia–c) into colourless 2:1-adducts, believed to have structure similar to VII or the corresponding cyclic saturated oxyphosphorane (VIII). The IR and NMR spectra of the adducts are in favour of the proposed structures.

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