Hg. Schwarz et E. Schaumann, GENERATION AND TRAPPING OF 1,3-DITHIAN-2-YLIDENE-SUBSTITUTED ETHYL CARBENE - ON THE EXISTENCE OF 4,8-DITHIASPIRO[2.5]OCT-1-ENE, Journal of the Chemical Society. Perkin transactions. I, (23), 1996, pp. 2773-2775
The readily available sodium salt of 2-(1,3-dithian-2-ylidene)acetalde
hyde tosylhydrazone 6 could be thermolysed to transient 2-(2-diazoethy
lidene)-1,3-dithiane 7 and from there to 1,3-dithian-2-ylidene-substit
uted ethyl carbene 8. Both species gave cycloadditions with different
types of alkenes. Evidence is presented for the electrocyclisation of
the vinyl carbene to 4,8-dithiaspiro[2.5]oct-1-ene.