The Journal of Organic Chemistry

Strained-ring systems. IV. The synthesis and solvolysis of exo-bicyclo [2.2. 0] hex-2-yl tosylate

RN McDonald, CE Reineke

Index: McDonald,R.N.; Reineke,C.E. Journal of Organic Chemistry, 1967 , vol. 32, p. 1878 - 1887

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Citation Number: 28

Abstract

The synthesis of bicyclo [2.2. 0] hex-2-ene and its hydroboration to ezo-bicyclo [2.2. 0] hexan- 2-ol (sa) is reported. Acetolysis of 5a tosylate produces 53% ion pair return to ezo-bicyclo [2. ll] hex-2-yl tosylate and an acetate mixture composed of 4-cyclohexenyl acetate (51%), eso- bicyclo [2. ll] hex-5-yl acetate (41%)] S-cyclohexenyl acetate (5%)), and eso-bicyclo [2.2. 0] hex-2-yl acetate (3%). Formolysis gave a similar distribution of products. It is concluded ...