Synthesis of in, out-bicyclo [4.4. 4] tetradecane. Generation of a stable. mu.-hydrido-bridged carbocation

JE McMurry, CN Hodge

Index: Mcmurray,J.E.; Hodge,C.N. Journal of the American Chemical Society, 1984 , vol. 106, p. 6450

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Citation Number: 45

Abstract

3 1 a (a)(EtO), P (O) CH, COOEt, NaH, THF;(b) LiAlH,, THF;(c) pyridinium chlorochromate, CH, Cl,, NaOAc;(d) H,, Pd/C, ethanol;(e) TiCl,, ZnCu, dimethoxyethane, A;(f) H,, PtO,, ether, 50 psi, 3 days. aldehyde 7 taking place in 30% yield to give in-bicyclo [4.4. 4]-1-tetradecene (3). 7 In addition to in-isomer 3, a small amount of isomeric product-presumably the corresponding out isomer-was detected by GC/MS. That the titanium-induced cyclization ...