By Frank Northen Magill
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Yamamoto, and M. Maeda, Chem. , 1981,1035. J. Wengrovius, J. Sancho, and R. R. Schrock, J. Am. Chem. ,1981,103,3932. B. Tarnchompoo, Y. Thebtaranonth, S. Utamapanya, and P. Kasemsri, Chem. , 1981, 1241. 2'4 Symmetrical diarylacetylenes (181) can be prepared in moderate yields by treating substituted p- nitrostyrenes (180) with hydrogen peroxide and triethylamine. 215 i-iii c1 c1 iv p ~ Ar Ar1-E- Ar2 Ar2 (179) Reagents: i. AlC1,-Ar'H; ii, Ar'H; iii, H20; iv, A120, R' (181) R' = H or OMe, R2 = OMe; R', R2= OCH2O Successive treatment of phenylacetylene with butyl-lithium and potassium t-butoxide leads to the ortho- metallated phenylacetylide (182).
1981, 22. 1451. Saturated and Unsaturated Hydrocarbons 45 Scheme 76 suitable reactants. 202High yields of allenylsilanes and sulphides, allenic acids and dialkylamides, and pallenic alcohols are available by this method. However, additions to ketones are less satisfactory since propargylic alcohols are formed in some cases. Propargyl iodides, formed in situ from the corresponding bromides, react successively with stannous chloride and aldehydes to give high yields of mixtures of a-hydroxyallenes and p- hydroxyacetylenes.
T. Sakakibara, I. Takai, E. Ohara, and R. Sudoh, J. Chern. , Chem. , 1981,261. D. G. Mislankar, B. Mugrage, and S. D. , 1981, 22, 4619. A. Millan, E. Towns, and P. M. Maitlis, J. Chem. , Chem. , 1981, 673. g. 89 //c' fi Si2Me6-Pd(PPh3), I R=HorMe SiMe, (62) Treatment of either 1- (63) or 3-trimethylsilylally1 acetate (64) with nucleophiles (enamines or sodium derivatives of active methylene compounds) in the presence of a catalytic mixture of Pd(PPh3)4and triphenylphosphine gives . g. (65),e x c l ~ s i v e l yThe almost the same whichever ally1 acetate is used, suggesting that the same intermediate T-allylpalladium complex is involved in each case.
A review of the literature published during 1981 by Frank Northen Magill