Premium
Dibenzo[ d,h ][1,3,6,7,2]dioxadithiasilonin: Synthesis and characterization
Author(s) -
Pastor Stephen D.,
Denney Dorothy Z.
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250259
Subject(s) - chemistry , triethylamine , iodine monochloride , sulfur , medicinal chemistry , zinc , ring (chemistry) , iodine , organic chemistry
The reaction of 2,4‐di‐ t ‐butylphenol, 4 , with sulfur monochloride gave the trithiobisphenol 5 rather than the expected dithiobisphenol 7 . The thiol 6 was obtained by the reduction of 5 with zinc under acidic conditions. The dithiobisphenol 7 was prepared by the oxidative coupling of 6 with iodine under alkaline conditions. The dibenzo[ d,h ][1,3,6,7,2]dioxadithiasilonin 8 was prepared by the reaction of 7 with dichlorodimethylsilane using triethylamine as an acid acceptor. No change was observed in the 1 H nmr spectrum of 8 upon cooling to −55°, which suggests that the ΔG* for ring inversion is less than the corresponding eight‐membered dibenzo[ d,g ][1,3,2]dioxasilocin and dibenzo[ d,g ][1,3,6,2]dioxathiasilocin 1 and 2 , respectively. The spectral data and elemental analysis are fully in accord with the nine‐membered silonin structure.