New generation and cycloaddition of α-(n-tert-butylimino)-o-quinodimethane

Add time:08/31/2019    Source:sciencedirect.com

CsF induced 1,4-elimination of ammonium bromide 7, prepared by quaternization of N-tert-butyl o-(dimethylaminomethyl)benzimidoylsilane 6, provides a new generation of α-(N-tert-butylimino)-o-quinodimethane (3a), which gives benzocyclobutenone N-tert-butylimine (8) in the absence of dienophile. Trapping of 3a with electron deficient olefins affords Diels-Alder adducts regioselectively.

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