Reaktionsgleichung
[Na+].[I-].CC(C)=[O:5].Br[C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[C:9]1=[C:18]1[CH:25]3[CH2:26][CH:21]4[CH2:22][CH:23]([CH2:27][CH:19]1[CH2:20]4)[CH2:24]3)[CH2:15]2>O.O1CCOCC1>[OH:5][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[C:9]1=[C:18]1[CH:25]3[CH2:26][CH:21]4[CH2:22][CH:23]([CH2:27][CH:19]1[CH2:20]4)[CH2:24]3)[CH2:15]2Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
The 4-eq.-bromoadamantylidene adamantane has bee found to have particularly advantageous and unexpected properties. Thus, unlike the corresponding 4-eq.-chloroadamantylidene adamantane, this compound permits carrying out substitution reactions by means of solvolysis without requiring an adjuvant such as an Ag+ salt. It has moreover been found that certain substituents can be introduced in one step where this had not been possible before. The 4-eq.-bromoadamantylidene adamantane reacts with primary and secondary alcohols to form ethers, with carboxylic acids to form esters, with primary amines to form secondary amines, and with nitriles to form N-adamantylidene adamantyl amides. Furthermore it has been found to be possible to carry out halogen exchange reactions with this compound, for example, in a reaction with NaI/acetone. Reaction of 4-eq.-bromoadamantylidene adamantane with H2O/dioxane gives a quantitative yield of 4-eq.-hydroxyadamantylidene adamantane. The solvolysis reactions are carried out in the pure reagent as the solvent or together with dioxane or DMF as a co-solvent.
Quellen und Nachweise
- ORD-Eintrag
- ord-7324533b08bd41688f73819b86471cf3
- Quelldatensatz
- uspto-grants-1987_11
- Patentnummer
- US04705847
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