Thermal rearrangements of azathiabenzenes; [1,4] shifts in cyclic sulphur–nitrogen ylides
Abstract
The azathiabenzene derivatives (3), (7), and (11) rearrange on heating by a [1,4] shift of the sulphur substituent ot carbon rather than a [1,2] shift to nitrogen, even though for ylides (3) this rearrangement involves loss of thiophen and furan aromaticity.