Preparation of S-arylsulfoniacyclane salts

Exclusive ortho substitution of phenols via [2,3]-sigmatropic rearrangements

“…When 17 was used with a l-equiv excess of o-cresol, we obtained 73% of 19 compared to a "best yield" of 45% by other methods. 11 The usefulness of this transformation is better appreciated when it is realized that Raney-nickel desulfurization of 19 gave 2-methyl-6-nbutylphenol (20) in 92% yield. Thus, the overall yield for the ortho n-butylation of o-cresol was 67%.…”

“…General Procedure. To a rapidly stirred solution of 0.980 g (5.0 mmol) of 0-acyl-2-methylthiomethylphenol in 20 mL of carbon tetrachloride at room temperature was added 0.70 g (5.25 mmol) of A'-chlorosuccinimide in one portion. After 1 h the succinimide was removed by filtration and the filtrate was concentrated in vacuo.…”