Potassium cyanide, reaction with epichlorohydrin

The earliest example of a Diels-Alder reaction of a 2-aminofuran was described by Johnson and Heeschen (64JOC3252), who found that the 3,4-dihydroaniline derivative 32 (Scheme 7) is formed in the reaction of epichlorohydrin with potassium cyanide. These workers rationalised the formation of product 32 in terms of transient formation of 2-aminofuran 103 which undergoes cycloaddition with its nitrile precursor (IIOCH2CH = CHCN) (see Scheme 7, Section II.B.l.d). 

Johnson and co-workenj1 36 have helpod to dariry the course of this reaction by carefully examining the distribution of products from the condensation of epichlorohydrin with aqueous potassium cyanide in buffered and in non-buffered solution. Although mixture was formed if a pH of 9.6 was maintained (Eq. 788a), only l,3-dicyano-2-... 

COPPER NITRATE or COPPER(n) NITRATE (3251-23-8) A strong oxidizer. Violent reaction with reducing agents, combustible materials, acetic anhydride, ethers, potassium ferrocyanide, finely divided tin. The aqueous solution is a medium-strong acid. Incompatible with bases, acetylene, ammonia, aliphatic amines, aikanolamines, amides, alkylene oxides, cyanides, epichlorohydrin, esters, isocyanates, organic anhydrides, vinyl acetate. Attacks metals in the presence of moisture. 

A common synthetic approach to GABOB uses epichlorohydrin (6.29) as a starting material. In a simple example, 6.29 was treated with potassium phthalimide and sodium cyanide to give GABOB (6.27), after hydrolysis and removal of the phthalimidoyl group.3 In one variation of this reaction, the intermediate phthal-imidoyl product was isolated prior to ti atment with cyanide. 2 The reaction can be... 

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