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) have been prepared and characterized by comprehensive spectroscopy and, in one case, an X-ray crystal structure determination. Pyrolysis of 2 leads to the corresponding 1,2,4-trithiolanes 3 after extensive sulfur scrambling. Addition of arenethiols to 2 (R5 = t-Bu), but not 2 (R5 = 1- adamantyl), leads to the corresponding adducts 13 with an unusual dithioacetal structure. Ozonolysis of 2 gives the corresponding alpha-diketones such as 16.