and refluxed until an aliquot of the resulting clear red solution showed no precipitate when drowned in water. About 650 mL of solvent was then distilled, and the remaining deep red liquid was drowned with 500 mL of water. The red solution was neutralized with 66 g (1.1 mol) of acetic acid and extracted with 1 L of hot heptane and then 300 mL. of cold heptane. The aqueous layer was made alkaline with 32 g of 50% aqueous NaOH, saturated with sodium chloride, and extracted with three 200-mL portions of 1,2-dichloroethane. Removal of the dichloroethane in vacuo gave 75 g (94%) of medium-red oil which was identical with the bis[ [(2-hydroxyethyl)thio]methyl] ether made from bis( chloromethyl) ether.Bis[(n-buty1thio)methylJ Ether. A solution of 12 g (0.13 mol) of butanethiol and 4.6 g (0.02 mol) of bis(phenoxymethy1) ether in 50 mL of DMF was treated with 2.9 g (0.13 mol) of sodium hydride and refluxed for 5 h at 150 "C. The resulting solution was drowned in water and taken up in 200 mL of ether. After the solution was washed with 20% aqueous NaOH and water, the solvent was removed, giving 5.4 g of an oily product shown by VPC to contain 70% bis[ (n-buty1thio)methyll ether (85% yield) and 30% butyl sulfide and disulfide. Analysis by NMR was consistent with that of authentic product prepared from butyl mercaptan and bis(bromomethy1) ether. 5,60-24-2; bis[[(2-hydroxyethyl)thio]methyl] ether, 36727-72-7; butanethiol, 109-79-5; bis[(n-buty1thio)methyll ether, 62609-74-9; bis-[(4-~hlorophenoxy)methyl] ether, 60093-88-1; bis[(2-chlorophenoxy)methyl] ether, 60093-87-0; bis[(2,4-dichlorophenoxy)methyl] ether, 60093-89-2; bis[ (2,3,4,5,6-pentafluorophenoxy)methyl] ether, 80484-50-0; bis[ (2,4,6-tribromophenoxy)methyl] ether, 61454-70-4; bis[(4-methylphenoxy)methyl] ether, 42818-09-7; bis[(a-methylphenoxy)methyl] ether, 42818-07-5; bis[ (4-methoxyphenoxy)methyl] ether, Four members of the new class of 2-silabicyclo[ 2.2.11 heptanes, or 2-silanorbornanes, were prepared: 2-silanorbornane (l), 2,2-dichloro-2-silanorbornane (2),2-chloro-2-methyl-2-silanorbornane (3), and 2-methyl-2-silanorbornane (4); the ring-closure reaction involved a platinum-catalyzed, intramolecular hydrosilation. The silanes were characterized by carbon and hydrogen elemental analyses and by 'H, 13C, and ' %i NMR, IR, and mass spectrometry. Isomer assignments for 3 and 4 were made on the basis of the NMR data. In the mass spectra, each compound gave an abundant molecular ion and a major mode of fragmentation peculiar to this bicyclic system. Some initial stereochemical studies of the reactions of 3 and 4 were performed, including fluoride-induced equilibration of the isomers of 4. (norbornanes) have provided great insight into the understanding of reaction mechanisms, spectral properties, and structure of organic molecules. As part of a program to prepare new organosilicons for study, we report the first unambiguous synthesis and characterization of 2-silabicyclo[2.2.1] heptane (l), or 2-silanorbornane, and some of its derivatives 1, X = Y = H 3 , X = M e ...