Malononitrile → Dihydro-2H-pyran-4,4(3H)-dicarbonitrile

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Reaction Steps

According to Flowchart B dichloroethyl ether (7) and malononitrile (8) are reacted with potassium carbonate in acetonitrile at reflux, giving tetrahydro-4H-pyran-4,4-dicarbonitrile (9) which is then reacted with 1N borane in tetrahydrofuran followed by treatment with hydrochloric acid, giving tetrahydro-4H-pyran-4,4-dimethanamine dihydrochloride (10) which is then reacted with sodium acetate and potassium tetrachloroplatinate in water, giving the product (11). ##STR7## In Flowchart C, compound 13 is derived by treating 12 with chlorine gas in dilute hydrochloric acid. ##STR8## In Flowchart D, compound 15 is derived by treating 14 with hydrogen peroxide.

Provenance & Evidence