REGIOCONTROLLED SYNTHESES OF SOME NEW SPIRO[POLYCYCLIC-1'-ISOTHIOCHROMAN]-4'-ONE DERIVATIVES

Indan-1-one (1a), 1-tetralone (1b), fluorenone (1c), and anthrone (1d) reacted with mercaptoacetic acid in toulene in the presence of p-tolu enesulfonic acid to give spiro[indan-1,2'-[1',3']oxathialan]-5'-one (2 a), trahydro-naphthalene-1,2'-[1,3']oxathialan]-5'-one (2b), spiro[flu orene9,2'-[1',3']-oxathialan]-5'-one (2c), and ro[anthracene-9(10H)-2' -[1',3']-oxathialan]-5'-one (2d), respectively. Compounds 2a-d reacted with arenes in the presence of aluminum chloride to yield spiro[polyc yclic-1'-isothiochroman]-4'-one derivatives 3a-t. The mechanisms of th ese reactions are discussed. All the synthesized spiroheterocycle deri vatives were identified by conventional methods (IR, H-1-NMR spectrosc opy) and elemental analyses. (C) 1996 John Wiley & Sons, Inc.