Abstract
2,6-Dichloro-9-thiabicyclo[3.3.1]nonane, easily available by an improved condensation of sulfur dichloride, sulfuryl chloride, and 1,5-cyclooctadiene, is a well- behaved scaffold for the nucleophilic substitution of azides and cyanides via neighboring- group participation by the sulfur atom. The products are isolated in high yields with purity >95% by simple extraction and washing protocols.
Highlights
The behavior of 2,6-dichloro-9-thiabicyclo[3.3.1]nonane (1) is a good example of the power of anchimeric assistance in organic chemistry [1]
We have found that the sequential treatment of diene with sulfur monochloride (S2Cl2) followed by sulfuryl chloride (SO2Cl2) provides high yields of 1 in a robust and convenient manner (Scheme 1) [1b]
The addition of sulfuryl chloride initiates a cascade of reactions that has the effect of providing an additional equivalent of chlorine
Summary
The behavior of 2,6-dichloro-9-thiabicyclo[3.3.1]nonane (1) is a good example of the power of anchimeric assistance in organic chemistry [1]. The transannular addition of SCl2 to 1,5-cyclooctadiene [4] gives 2,6-dichloro-9thiabicyclo[3.3.1]nonane (1) in excellent yield at a variety of concentrations and scales, but the reaction was successful (at least in our hands) only when the hazardous reagent SCl2 was purified by careful double distillation just before use [5]. We have found that the sequential treatment of diene with sulfur monochloride (S2Cl2) followed by sulfuryl chloride (SO2Cl2) provides high yields of 1 in a robust and convenient manner (Scheme 1) [1b].
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