Formation and Mechanistic Implication of a Novel Thiaazabicyclooctane Derivative During the Cycloaddition of N-Acetyl Cinnamic Acid Thioamide

Article abstract of DOI:10.1016/S0040-4039(00)74373-5

In the course of synthesizing thiopyran 3a, the novel thiaazabicyclooctane 8, a precursor to 3a, has been isolated as a major product.The formation of 8 provides further insight into the mechanism of the <4+2> cycloaddition involving 1a, which we have previously discussed to be an efficient way of generating usefully functionalised dihydrothiopyrans.The structure of compound 8 was established by detailed NMR investigations.