10.1021/acs.organomet.6b00208.s003 Chenting Yan Chenting Yan Zheng Xu Zheng Xu Xu-Qiong Xiao Xu-Qiong Xiao Zhifang Li Zhifang Li Qiong Lu Qiong Lu Guoqiao Lai Guoqiao Lai Mitsuo Kira Mitsuo Kira Reactions of an Isolable Dialkylstannylene with Carbon Disulfide and Related Heterocumulenes American Chemical Society 2016 distanna ArN Carbon Disulfide isomeric mixture column chromatography Compounds 8 Stannylene 1 isolable dialkylstannylene 1 Lewis acid CO 2 reaction conditions NMR spectroscopy CS 2 DFT calculations Isolable Dialkylstannylene Related Heterocumulenes 2016-04-21 13:06:22 Dataset https://acs.figshare.com/articles/dataset/Reactions_of_an_Isolable_Dialkylstannylene_with_Carbon_Disulfide_and_Related_Heterocumulenes/3188008 The reaction of isolable dialkylstannylene <b>1</b> with an excess amount of CS<sub>2</sub> produces an isomeric mixture of 3,3′-distanna-2,2′,4,4′-tetra­thia­bicyclo­butylidene <b>8</b> and 3,7-distanna-2,4,6,8-tetra­thia­bicyclo­[3.3.0]­oct-1(5)-ene <b>9</b> with a ratio depending on the reaction conditions. Compounds <b>8</b> and <b>9</b> are separated by column chromatography and characterized by NMR spectroscopy and X-ray crystallography. Detailed investigation of the reaction has revealed that the initial product is <b>8</b>, which isomerizes to <b>9</b> irreversibly under the catalytic influence of <b>1</b> as a Lewis acid. The above view is supported by the theoretical DFT calculations. Treatment of <b>1</b> with ArNCO [Ar = 2,6-<i>i</i>Pr<sub>2</sub>C<sub>6</sub>H<sub>3</sub>] affords the corresponding carbamoyl­(hydroxyl)­stannane <b>11</b> via the hydrolysis of the corresponding sila­aziridinone formed by the [1 + 2] cycloaddition reaction of <b>1</b> with the NC double bond of the isocyanate. Stannylene <b>1</b> reacts with ArNCS, giving a mixture of complex products, while <b>1</b> does not react with CO<sub>2</sub>.