Epichlorohydrin, reaction with cyanide

The early literature of epoxide chemistry contains several accounts of the reaction of hydrogen cyanide with epichlorohydrin, 11-1T1 epibromohydrin,10 ethyl glycidyl ether,J- and related substance Attack by the nucleophilic aperies, CN- ion in this case, occurs uniquely at the site furthest from the polar atom,. e. at the terminal epoxidi-carbon atom (Eq. 787), An important contribution was made by... 

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). 

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