Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines
Copyright policy )Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines
A straightforward and novel method for transformation of readily available 1,3-benzoxazines to secondary phosphonates and α-aminophosphonates using boron trifluoride etherate as catalyst is developed. The formation of phosphonates proceeds through ortho-quinone methide (o-QM) generated in situ, followed by a phospha-Michael addition reaction. On the other hand, the α-aminophosphonates were obtained by iminium ion formation and the subsequence nucleophilic substitution of alkylphosphites. This method can be also used for the preparation of o-hydroxybenzyl ethers through oxa-Michael addition.
o-quinone methide, Magnetic Resonance Spectroscopy, <i>o</i>-quinone methide, Molecular Structure, phosphonates, Organophosphonates, Organic chemistry, Article, Catalysis, Benzoxazines, o-hydroxybenzylic ethers, 1,3-benzoxazines, QD241-441, <i>o</i>-hydroxybenzylic ethers, α-aminophosphonates
o-quinone methide, Magnetic Resonance Spectroscopy, <i>o</i>-quinone methide, Molecular Structure, phosphonates, Organophosphonates, Organic chemistry, Article, Catalysis, Benzoxazines, o-hydroxybenzylic ethers, 1,3-benzoxazines, QD241-441, <i>o</i>-hydroxybenzylic ethers, α-aminophosphonates
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