MOLECULAR ASSOCIATION OF 2,3-DIHYDRO-2-ALKYL-3-HYDROXYBENZISOTHIAOLE 1,1-DIOXIDES - FORMATION OF NOVEL BICYCLIC DIMERS CONTAINING 12 14-MEMBERED RINGS/

2,3-Dihydro-3-hydroxybenzisotkiazole 1,1-dioxides constitute a self-co mplementary hydrogen-bond donor-acceptor system. 2,3-Dihydro-2-isoprop yl-3-hydroxybenzisothiazole 1,1-dioxide exhibits interesting concentra tion and temperature-dependent NMR spectra due to association in solut ion. The intermolecular association of these molecules through S-O ... H-O interactions resulting in the formation of novel hydrogen-bonded dimers containing 12/14-membered bicyclic bridge is revealed by X-ray crystallography. X-ray crystallographic studies also confirm the exist ence of N-alkyl-2-formylbenzenesulfonamides exclusively as 2,3-dihydro -2-alkyl-3-hydroxybenzisothiazole 1,1-dioxides in the solid state.