Rearrangement of Dimethyl(furylmethyl)ammonium and Dimethyl(thienylmethyl)ammonium N-Methylides. Isolation and Reaction of Nonaromatic Intermediates

Article abstract of DOI:10.1021/jo00046a025

3-<(Dimethylamino)methyl>-2-methylene-2,3-dihydrofuran (5o) and 2-<(dimethylamino)methyl>-3-methylene-2,3-dihydrofuran (12o) and their thiophene analogues 5s and 12s were prepared in high yields by fluoride-ion induced desilylation of N,N-dimethyl-N-<(trimethylsilyl)methyl>(2-furylmethyl)ammonium (3o) and -(3-furylmethyl)ammonium iodides (10o) and their thienylmethyl analogues 3s and 10s.Compound 5s or 12s was successfully converted to 3-<(dimethylamino)methyl>(2-thienylmethyl)lithium (23s) or 2-<(dimethylamino)methyl>(3-thienylmethyl)lithium (26s), which reacted with aldehydes to give <(dimethylamino)-methyl>(2-hydroxyalkyl)thiophenes 25s or 27s, respectively.