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Most potent antioxidants possess one of the two structurcs, ArOH or ArNHR. The 1:tbilc hydrogetis have beell viewccl as a critical part of the structures and characterization of inhibition products shows that they arc indeed removed durillg the course of the reactions. However, several lines of evidcncc indicate that hydrogcii abstraction is not a discrcte first step in the inhibition process. The key observations are: (1 ),there is 110 kinetic isotope effect noted if S-D-S-methyl;Lililine and N-D-diphenylamine are compared with the corresponding undeuterdtcd aminc; (2 j specifically designed compou~ids such as hydrazobenzene, do not prove to be as potent as inhibitors as their close relatives despite the fact that the former apparently should have a good aptitude for the hydrogen abstraction reaction; ( 3 ) the effects of substitueiits 011 the inhibitory efficiency of aromatic amines and phenols can be correlated with the Hamniett equation in a mariner which suggests that electron removal from the inhibitor is of paramount importance; (4) despite the absence of labile hydrogens dimethylaniline shows distinct, but weak, inhibitory action and N,S'-tetramethyl-~-plieii~letiedi~mii1c is a strong inhibitor; a d ( 5 ) it has been found that the latter compound is converted to a complex which may be hydrolyzcd to form a Wurster dye. These data are held to be consistent with the view that the first stcp of the inhibition process is the reversible formation of a loosc molecular complex betwecii the inhibitor and ROr.. This complex then is destroyed by reaction with a second ROz. radical.

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A typical duplicate run yielded 52.5% of VII, b.p. 94-97' (0.10 mm.), 71% 1.4853. E. Proof of Structure for the Cyclic Formal of cis-3,a-Dihydroxycyclohexylmethanol (IV). 1. Methylation of 5-Hydroxymethylhexahydrobenzo-cis-1,3-dioxole (VII) .-In a microreaction flask waa heated 0.6 g. (0.026 g.-atom) of sodium metal in 30 ml. of toluene. To the sodium at reflux was added dropwise over 45 min. a solution of 4.00 g. (0.0254 mole) of VI1 in 20 ml. of toluene (Nz atmosphere). The formation of the alkoxide waa allowed to proceed overnight. After 14 hr., dimethyl sulfate, 3.2 g . (0.025 mole) in 10 ml. of toluene, waa added over 15 min. and the reaction mixture allowed to reflux 2 hr. Methanol, 10 ml., waa added and the resulting toluene solution washed with dilute ammonia water and dried over anhydrous sodium sulfate. After removal of the solvent the residue waa distilled. One main fraction was collected, 3.0 g. (73q;b yield), of 5-methoxymethylhexahydrobenzo-cis-l,3-dioxole, b.p. 58' (0.1 mm.), n * '~ 1.4605.Anal. Calcd. for CoHieOj: C, 62.76; H, 9.34. Found: C , 62.45; H, 9.37. 2. Hydrolysis of the Methylated Formal of IV and Determination of 1,2-Glycol Content.-A 0.2811-g. sample of the methylated formal of IV, 50 ml. of water, and 5 drops of concentrated HC1 were heated on a steam bath overnight. The reaultant homogeneous solution waa diluted quantitatively to 100 ml. and the concentration of 1,2-glycol structure determined by periodic acid titration.' Aliquota of the hydrolyzed glycol took up 98-110% of the theoretical amount of periodic acid after a 1-hr. reaction time a t 25'.Acknowledgment.-The trans-hexahydrobenzo-l,3dioxole wm synthesized for the first time by Dr. Newman M.Propanesultam has been prepared by addition of thiolacetic acid to allyl chloride, oxidation of the adduct with aqueous chlorine to 3-chloropropanesulfonyl chloride, reaction with ammonia, and cyclization of the resulting 3chloropropanesulfonamide in alcoholic base. Chromatographically pure propanesultam had m.p. 23.1-23.2', b.p. 156-157 (2 mm.), n% 1.4826; the N-benzoyl derivative melted a t 171-172'. Polymerization of propanesultam of 99.17, purity has been investigated using a variety of catalysts. Basic catalysts such aa sodium hydride, sodium and potassium hydroxides, potassium phenoxide, or tetramethylguanidine are effective in producing polymer of high molecular weight, m.p. 257-260°, [ q ] 0.77 dl./g., particularly when used with an N-alkane-or N-arenesulfonyl-l,3-propaneaultam aa cocatalyst, as for example, N-(p-toluenesulfonyl)-1,3-propanesultam.Octadecylamine hydrochloride, aniline hydrochloride, picric acid, p-toluenesulfonic acid, mesitylenesulfonic acid, and benzenesulfonyl chloride effected polymerization, but only polymer of low molecular weight waa produced.Lewis acids were ineffective under a variety of conditions.

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