Synthesis of organophosphorus derivatives of 2,6‐di‐tert‐butyl‐4‐methylphenol

Abstract

Convenient procedures for the synthesis of 2,6-di-tert-butyl-4-methylphenol (ionol)

Synthesis of mono‐ and bisorganophosphorus substituted amides of unsaturated carboxylic acids with PCHNC(O) and antioxidant fragments

“…(N-methyl-N-cinnamoyl)methylphosphonate (6). A solution of 6 g of phosphonate 5 in 10 mL of diethyl ether was added with stirring and cooling at 10…”

“…Also recently, we have proposed the convenient methods for the synthesis of new functionalized mono-and bisorganophosphorus compounds including ionol fragments [6], which were used by us for preparation of stable phenoxyl radicals [7] and were possessed of antioxidative activity [8]. In this work, we propose the unique way for the synthesis of new monoand bisorganophosphorus substituted amides of unsaturated carboxylic acids with PCHNC(O) and antioxidant fragments (cf.…”

Synthesis of new functionalized mono‐ and bisorganophosphorus acids and their derivatives with unsaturated and aromatic fragments

“…The mixture was refluxed until ammonia no longer evolved and then distilled to obtain 26.4 g of phosphonite 1 (see Table 1). (4). A mixture of 8.3 g ammonium hypophosphite, 22.4 g of benzaldehyde, and 40 g of chlorotrimethylsilane in 60 mL of methylene chloride was heated under reflux with stirring for 2 h. Ammonium chloride was filtered off and 60 mL ethanol was added to the residue.…”

“…Various derivatives of substituted hydroxymethylenebisphosphonic acids are good complexones and widely used in medicine [1][2][3]. Recently, we have proposed convenient procedures for synthesis of a series of organophosphorus derivatives of 2,6-di-tert-butyl-4-methylphenol (ionol) with one, two, or three phosphoruscontaining groups [4,5]. These compounds were used by us for the preparation of stable phenoxyl radicals [6] and were interesting as effective antioxidants with the multifunctional mode of action [7].…”

Synthesis of Organophosphorus‐Substituted Amides of Carbonic Acids with PCHNC(O) and 2,6‐Di‐tert‐butyl‐4‐methylphenol Fragments

“…Also recently, we have proposed the convenient methods for synthesis of new functionalized organophosphorus compounds including of ionol fragments [3,4], which were used by us for preparation of stable phenoxyl radicals and were possessed of antioxidative activity [5]. In this work, we propose the unique way for synthesis of new organophosphorus-substituted amides of various carbonic acids with PCHNC(O) and ionol fragments, which was based on available imines [6,7], acyl chlorides [8], and trimethylsilyl esters of trivalent organophosphorus acids [9].…”