反応式
Br/[CH:2]=[CH:3]\[CH3:4].[CH2:5]=[CH:6][C:7](=[CH2:9])[CH3:8].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>>[CH3:9][C:7](=[CH:6][CH2:5][CH:2]=[CH:3][CH3:4])[CH2:8][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1参加物
実験手順
In a much slower reaction than Example 19, Z-1-bromopropene, isoprene and morpholine gave 2-methyl-1-morpholino-2,5-heptadiene in 40% yield along with higher boiling unidentified products and polymers. The major point of interest in this Example was to determine whether or not the stereochemistry of the Z-1-bromopropene was retained in the product. The product appeared homogeneous by GLC (gas liquid chromatography) and NMR (nuclear magnetic resonance); however, IR (infrared) showed bands characteristic of both cis and trans olefinic groups. Therefore, the product may be a mixture of isomers. Aside from the stereochemistry with respect to the double bonds, the structure can be assigned conclusively from the NMR spectrum. The addition of the 1-propenyl group, therefore, was completely regio-selective, adding to the terminal carbon of the less-substituted double bond of the isoprene. This contrasts with the mixture of positional isomers obtained when this halide was added to 1-hexene (refer Example 4, supra).
出典と根拠
- ORDレコード
- ord-22f6ea37883c402c8e5658450265b140
- 出典データセット
- uspto-grants-1979_11
- 特許番号
- US04175187
関連ノート
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