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• W2950992810 abstract "The reactions of (E)-1-(phenylseleno)-2-(trimethylsilyl)ethene (1a) and (E)-1-(phenylseleno)-2-(triethylsilyl)ethene (1b) with dimethyl 1,1-dicyanoethene-2,2-dicarboxylate (2) in the presence of SnCl4 in CH2Cl2 at −78 °C for 1 h exclusively afforded [2 + 2] cycloadducts 3a and 3b in 71% and 78% yields, respectively. The exclusive [2 + 2] selectivity in the reaction of 1 with 2 in the presence of SnCl4 is explained by destabilization of the proposed selenium-bridged intermediate that would lead to the [2 + 1] adduct by the presence of the two electron-withdrawing cyano groups. The reaction of 1a with 2 at 0 °C to room temperature in the presence of ZnBr2 gave a regioisomeric [2 + 2] cycloadduct 7a in low yield along with a corresponding desilylated cyclobutane 8 as the major product in moderate to good yield. The origin of the Lewis acid dependence of the regioselectivity was deduced from a theoretical comparison of stability of Lewis acid complexes." @default.
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• W2950992810 date "1998-04-23" @default.
• W2950992810 modified "2023-10-09" @default.
• W2950992810 title "A Novel Strategy for Cyclobutane Formation. Fine Tuning of Cyclobutanation vs Cyclopropanation" @default.
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• W2950992810 doi "https://doi.org/10.1021/jo972310e" @default.
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