Sterically Hindered Aromatic Compounds. III. Acid-catalyzed Reactions of 2, 4, 6-Tri-t-butyl-and 2-Methyl-4, 6-di-t-butylbenzyl Alcohols and Chlorides

LRC Barclay, HR Sonawane…

Index: Barclay,L.R.C. et al. Canadian Journal of Chemistry, 1972 , vol. 50, p. 281 - 290

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Citation Number: 18

Abstract

Treatment of 2, 4, 6-tri-t-butylbenzyl alcohol (2), the corresponding benzyl chloride (3) and methyl ether (5) with strong acids gave high yields of 1, 1-dimethyl-4, 6-di-t-butylindane (10). On the other hand, acid-catalyzed reactions on 2-methyl-4, 6-di-t-butylbenzyl alcohol (13), chloride (16), and methyl ether (12) yielded nucleophilic substitution products. According to comparative hydride transfer reactions between triethylsilane and carbonium ions ...