Pentene Sodium methoxide

Perfluoro-2 (1 ethyl 1 methylpropyl)-3-methyl-l-pentene, the major hex-amer of tetrafluoroethylene, reacts with sodium methoxide to yield an ester, whereas a stable crowded ketene is formed by reaction with sodium hydroxide [2d] (equation 23)... 

Rase-catalyzed reaction of alcohol favors addition, whereas increasing amounts of alkoxide favor addition-elimination reactions. Perfluoro-2-methyl-2-pentene and methanol form the saturated ether, whereas two equivalents of sodium methoxide form the vinylic ether [S] (equation 4). 

Methanol, Hydrogen, Raney nickel catalyst, 0484 Methoxyacetyl chloride, 1165 4-Methoxy-3-nitrobenzoyl chloride, 2916 Methyl formate, Methanol, Sodium methoxide, 0834 3-Methyl-2-penten-4-yn-l-ol, 2384 Nitric acid, 4436... 

Fithium tetrahydroaluminate, Fluoroamides, 0075 Lithium tetrahydroaluminate, Water, 0075 Lithium, 1,2-Diaminoethane, Tetralin, 4675 Magnesium, Barium carbonate, Water, 4685 Maleic anhydride, Bases, or Cations, 1400 Mercaptoacetonitrile, 0763 t Methanol, Hydrogen, Raney nickel catalyst, 0482 4-Methoxy-3-nitrobenzoyl chloride, 2911 Methoxyacetyl chloride, 1161 t Methyl formate, Methanol, Sodium methoxide, 0830 3-Methyl-2-penten-4-yn-l-ol, 2378 Nitric acid, 4430... 

In the Bamford-Stevens reaction,2 sodium methoxide is commonly used as base. Kirmse et al.m have shown that use of sodamide or sodium hydride converts tosyl-hydrazones of aliphatic ketones and cyclic ketones into 1-olefins. Thus the tosyl-hydrazone of pentanone-2 gives pentene-1 in 83% yield together with small amounts of cis- and trans-pentene-2. 

The action of sodium methoxide on the tetraacetate of 1-nitro-l-hexene-D-arahino-3,4,5,6-tetrol (193) and the triacetate of 1-nitro-l-pentene-D-ery hro-3,4,5-triol (195) gave, as preponderant products, l-deoxy-2-O-methyl-l-nitro-D-mannitol (194) and l-deoxy-2-O-methyl-1-nitro-D-ribitol (196), respectively.172 As illustrated for the latter example, the configuration of the favored product is that which is expected in terms of approach of the addend from the less-hindered side (Cram s rule). 

The relative amount of base has a significant effect on the product distribution. When the tosyl hydrazone of pinacolone was treated with > 1.8 equivalents of n-butyllithium, 3,3-dimethyl-l-butene was formed. When only 1 equivalent of n-butyllithium was used, however, a 57% yield of 3,3-dimethyl-l-butene, 40% of 1,1,2-trimethylcyclopropane, and 3% of the rearranged alkene (2,3-dimethyl-1-butene) were isolated.264 jhe type of base employed is also important. The product distribution from the hydrazone of cyclopentanone, for example, gave a mixture of cyclopentene/( )-2-pentene/(Z)-2-pentene.265 When sodium methoxide was used, a 2 84 14 mixture of these products was obtained whereas sodium hydride led to a 83 14 3 mixture and sodium amide a 60 35 3 mixture.265... 

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