Tetrahedron

Stereospecific alkylation of benzene with (+)-propylene oxide by Lewis acid catalyst and stereochemistry of ring-opening

T Nakajima, S Suga, T Sugita, K Ichikawa

文献索引：Nakajima,T. et al. Tetrahedron, 1969 , vol. 25, p. 1807 - 1816

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被引用次数: 39

摘要

The alkylation of benzene with (+)-propylene oxide (I) in the presence of Lewis acid gave (+)- 2-phenyl-1-propanol (II), and a mixture of (−)-1-halo-2-propanol (III or V) and (+)-2-halo-1- propanol (IV or VI) as the by-products. The reaction was conducted under various conditions. The magnitude of the optical yields of these products suggests that both the alkylation and ring opening proceed with complete inversion of configuration and the most ...