FURTHER OBSERVATIONS ON RHCL3 ALIQUAT-336 CATALYZED CARBONYLATION OF AROMATIC DIYNES UNDER PHASE-TRANSFER CONDITIONS

The ion pair [(C8H17)3NMe]+[RhCl4(H2O)2]-, formed from aqueous rhodium trichloride and Aliquat 336(R), catalyzes the reductive double carbonylation of 1-phenylethynyl-2-(1-propynyl)benzene, 1, to give under phase transfer conditions 3-methyl-4-[2-(phenylethynyl) phenyl]-2(5H)furanone, 6. Under the same conditions 1,8-bis(ethynyl)naphthalene derivatives 8-11 are mono-carbonylated to form either monomeric or dimeric versions of 8-cyclopent[a]acenaphthylenones. The structures of the final carbonylation products depend on the nature of the substituents in 8-11. X-Ray diffraction analyses of the monomeric carbonylation products of 1,8-bis(trimethylsilyl) naphthalene, 13, and of the diketone, 16, resulting from 1,8-bis (1-octynyl)-naphthalene, are presented.