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Scheme 5 8 ) . g. ’” Although many substitution patterns are tolerated in either 14’ 14’ K. Nickisch, W. Klose, E. Nordhoff, and F. Bohlmann, Chem. , 1980,113, 3086. M. Lang, K. Prasad, J. Gosteli, and R. B. Woodward, Helv. Acta, 1980, 63, 1093. A. Alexakis, G. Cahiez, and J. F. Normant, Tetrahedron, 1980,36, 1961. C. Germon, A. Alexakis, and J. F. , 1980, 21,3763. C . Sreekumar, K. P. Darst, and W. C. Still, J. Org. , 1980, 45, 4260. HF Scheme 59 reactant, branching at the carbon p- to phosphorus in the ylide, or at the a'-position of the carbonyl partner, tend to diminish stereoselectivity.

1980, 10, 933. A. Gupta, K. Sacks, S. Khan, B. E. Tropp, and R. Engel, Synrh. , 1980,10, 299. -J. Tilhard, H. Ahlers, and T. , 1980, 21, 2803. Saturated and Unsaturated Hydrocarbons a XCHZPOPh;! g. g. 12' Both processes are compatible with cyano and ester groups, and when terminal silicates are used stereoselectivity is very high (>99%). Primary alcohols give the highest yields of enol ethers, whereas tertiary alcohols do not react, and allylic alcohols give the particularly useful ally1 vinyl ethers.

G. Scheme 3 5 ) . When sodium acetylide is used as a nucleophile the products are 1,3-enynes. '~~ The reagent, which is prepared in situ from tetraethylammonium bromide and hydrogen bromide, also hydrobrominates acetylenic alcohols and ethers. g. Scheme 36). g. (30)]. '11 lo' 'lo '" D. L. Reger and P. J. McElligott, J. A m . Chem. ,1980, 102, 5923. J. Cousseau, Synthesis, 1980, 805. E. J. Corey and H. , 1980, 21, 1113. I. Fleming and F. Roessler, J. Chem. , Chem. , 1980, 276. ^'^ 1-Oxoalkylphosphonates failed to react with other Wittig or Horner reagents.

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