The Journal of Organic Chemistry

Sodium nitroprusside-mediated substitution of oxygen for nitrogen at saturated carbon centers

GJ McGarvey, M Kimura

Index: McGarvey, Glenn J.; Kimura, Masayuki Journal of Organic Chemistry, 1986 , vol. 51, # 20 p. 3913 - 3915

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Citation Number: 11

Abstract

1s 20 Reagents ( a ) NaI04. HOAC-H~O (211 v / v ) ; O OC . 6 min; 0-20 OC. 5 min; 22 OC. 18 min; ( b ) Pb(OAc)4 (1.15 equiv).CH30H-benzene (111 v/v); 0 OC. 1.2 h; room temperature, 0 . 5 h; ( c ) HOAc/ concentrated HCI (1/3 v/v),4 h reflux; (d) CH2N2, CH3OH. however, was able to cleave simple benzoquinones to cis- muconic acid dimethyl esters using lead tetraacetate, and an earlier Italian paper16 describes the use of the same reagent for the ...

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