New reactions of thione S-(tert-alkylimides)

Two new alpha-chloro sulfenyl chlorides 1, four new 2-thioxo-1-tetralone S- imides 2 (X = CH2), and one new 3-thioxochroman-4-one S-imide 2 (X = O) hav e been prepared and characterized by comprehensive spectroscopy and, in one case, an X-ray crystal structure determination. Pyrolysis of 2 leads to th e corresponding 1,2,4-trithiolanes 3 after extensive sulfur scrambling. Add ition of arenethiols to 2 (R-5 = t-Bu), but not 2 (R-5 = 1-adamantyl), lead s to the corresponding adducts 13 with an unusual dithioacetal structure. O zonolysis of 2 gives the corresponding alpha-diketones such as 16.