The Reaction of Saccharin Derivatives with N,N-Diethylprop-1-ynamine: Formation of Cyclobutenyl Saccharinates and of a Spiro-oxete

Article abstract of DOI:10.1039/c39840001583

Saccharin and two equivalents of N,N-diethylprop-1-ynamine give a cyclobutenyl saccharinate (4) which, on bromination, gives the N-(cyclobutenyl cation)saccharin derivative (8), whose structure was established by X-ray crystallography ; N-methylsaccharin reacts with one equivalent of ynamine to yield the spiro-oxete (9): this represents the second isolation of such a stable oxete from reaction of an ynamine with a carbonyl group.