Hydrogen participation vs. elimination. The role and fate of neighboring hydrogen in solvolysis of neomenthyl tosylate

S Hirsl-Starcevic, Z Majerski…

文献索引：Hirsl-Starcevic, Sanja; Majerski, Zdenko; Sunko, Dionis E. Journal of Organic Chemistry, 1980 , vol. 45, # 17 p. 3388 - 3393

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被引用次数: 1

摘要

Product composition and ad1 and P-d3 isotope effects in the solvolysis of neomenthyl tosylate (8-OTs) were determined in 70% aqueous trifluoroethanol and 70% aqueous ethanol. Both trifluoroethanolysis and ethanolysis gave I-2% neomenthol (97% d3), 12-13% cis-4-menthanol (l00% d3), 2-3% trans-4-menthanol (lOO% d3), 66-70% 3-p-menthene (83% d3 and 17% dz), and 5-9% 4, 8-p-menthene (97% d3), respectively. These results ...