Reaction of 4-Benzoyloxy-l-oxyl-2,2,6,6- tetramethylpiperidine with Trimethylene Glycol 

Aqueous hydrogen peroxide is added to a mixture of 4-benzoyloxy-l-oxyl-2,2,6,6-tetramethylpiperidine and fer› rous chloride tetrahydrate in trimethylene glycol according to the procedure of Example 25. 

Tributyltin hydride is added dropwise to a solution of 2-iodoethanol and excess bis(l-oxyl-_2,2,6,6- tetramethylpiperidin-4-yl) sebacate in chlorobenzene. The crude reaction mixture is passed through silica gel with heptane and then heptane/ethyl acetate to afford the title compound. 

Reaction of Bis(l-oxyl-2,2,6,6-tetramethylpiperidin- 4-yl) Sebacate with Isopropanol 

Aqueous hydrogen peroxide is added to a mixture of bis(l-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) sebacate and ferrous chloride tetrahydrate in isopropanol according to the procedure of Example 25. 2 

Aqueous hydrogen peroxide is added to a mixture of 4-benzoyloxy-l-oxyl-2,2,6,6-tetramethylpiperidine and fer› rous chloride tetrahydrate in 1,4-butanediol according to the procedure of Example 25. 

Aqueous hydrogen peroxide is added to a mixture of 4-hexyloxy-l-oxyl-2,2,6,6-tetramethylpiperidine and fer› rous chloride tetrahydrate in pinacol according to the pro› cedure of Example 25. 

Reaction of l-Oxyl-2,2,6,6-tetramethylpiperidin-4- one with Glycerol 

Aqueous hydrogen peroxide is added to a mixture of l-oxyl-2,2,6,6-tetramethylpiperidin-4-one and ferrous chlo› ride tetrahydrate in glycerol according to the procedure of Example 25. 

Reaction-of-4-Hydroxy-l-oxyl-2,2,6,6- tetramethylpiperidine with 2-Ethyl-1-hexanol 

Aqueous hydrogen peroxide is added to a mixture of 4-hydroxy-l-oxyl-2,2,6,6-tetramethylpiperidine and ferrous chloride tetrahydrate in 2-ethyl-1-hexanol according to the procedure of Example 25. 

l-(2-Hydroxy-2-methylpropoxy)-4- hexadecanoyloxy-2,2,6,6-tetramethylpiperidine 

A mixture of 12.11 g (49.4 mmol) of the compound obtained in Example 16A, 12.11 g (44.8 mmol) of methyl 

Bis[ 1-(2-hydroxyethoxy )-2,2,6,6- tetramethy lpiperidin-4-y l] Sebacate 

Reaction of 4-Benzoyloxy-l-oxyl-2,2,6,6- tetramethylpiperidine with 1,4-Butanediol 

Reaction of 4-Hexyloxy-l-oxyl-2,2,6,6- tetramethylpiperidine with Pinacol 

## EXAMPLE 37 

## EXAMPLE 38 

## EXAMPLE 39 

## EXAMPLE 40 

## EXAMPLE 41 

## EXAMPLE 42 

## EXAMPLE 43 

## EXAMPLE 44 

hexadecanoate (methyl palmitate), 0.76 g of lithium amide, and toluene is heated at reflux. Methanol is distilled from the reaction mixture along with some of the toluene. The reaction mixture is quenched with dilute acetic acid, and washed successively with aqueous methanol, dilute aqueous sodium bicarbonate solution, and saturated sodium chloride solution. The toluene solution is dried over magnesium sulfate, filtered, and concentrated to obtain a solid. Purifi› cation by flash chromatography on silica gel with hexane/ ethyl acetate affords 18 g of a solid. Recrystallization from methanol yields 10.7 g of the title compound as a white solid, mp 60---64. 

1-(2-hydroxy-2-methylpropoxy )-4-eicosanoyloxy-2, 2,6,6-tetramethylpiperidine 

A mixture of 8.40 g (34.2 mmol) of the compound obtained in Example 16A, 10.17 g (31.1 mmol) of methyl eicosanoate, 0.35 g of lithium amide, and toluene is heated at reflux. The reaction mixture is quenched with dilute acetic acid, and washed successively with aqueous methanol, dilute aqueous sodium bicarbonate solution, and saturated sodium chloride solution. The toluene solution is dried over magnesium sulfate, filtered, and concentrated to obtain a solid which is purified by flash chromatography on silica gel with hexane/ethyl acetate to afford 9.9 g of the title com› pound as a white solid, mp 69-73. 

1-(2-hydroxy-2-methy lpropoxy )-4-(2- ethy lhexanoyloxy )-2,2,6,6-tetramethylpiperidine 

A mixture of 51.6 g (0.210 mol) of the compound obtained in Example 16A, 30.6 g (0.193 mol) of methyl 2-ethylhexanoate, 1.26 g of lithium amide, and toluene is heated at reflux. Methanol is distilled from the reaction mixture along with some of the toluene. The reaction mixture is quenched with dilute acetic acid, and washed successively with aqueous methanol, dilute aqueous sodium bicarbonate solution, and saturated sodium chloride solu› tion. The toluene solution is dried over magnesium sulfate, filtered, and concentrated to obtain a yellow liquid. Purifi› cation by flash chromatography on silica gel with hexane/ ethyl acetate affords 51.0 g of the title compound as a pale yellow oil. 

1-(2-hydroxy-2-methylpropoxy )-4-dodecanoy loxy-2, 2,6,6-tetramethylpiperidine 

A mixture of 72.7 g (0.297 mol) of the compound obtained in Example 16A, 51.9 g (0.242 mol) of methyl dodecanoate (methyl laurate), 0.43 g of lithium amide, and toluene is heated at reflux. Methanol is distilled from the reaction mixture along with some of the toluene. The reaction mixture is quenched with dilute acetic acid, and washed successively with aqueous methanol, dilute aqueous sodium bicarbonate solution, and saturated sodium chloride solution. The toluene solution is dried over magnesium sulfate, filtered, and concentrated to obtain a solid. Purifi› cation by flash chromatography on silica gel with hexane/ ethyl acetate affords 96.7 g of the title compound as a white solid, mp 46-8. 

Reaction of N,N’,N" ,N"’-Tetrakis{2,4-bis[N-(1-oxyl- 2,2,6,6-tetramethylpiperidin-4-yl]butylamino ]-s› triazin-6-y 1 }-3,3 ’-ethy lenediiminodipropylamine with Cyclohexanol 

A mixture of N,N’,N" ,N"’-tetrakis{2,4-bis[N-(1-oxyl-2,2, 6,6-tetramethy lpiperidin-4-y 1 ]buty lamina ]-s-triazinyl }-3,3’- 

## EXAMPLE 44A 

## EXAMPLE 44B 

## EXAMPLE 44C 

## EXAMPLE 45 

