title: Spontaneous dimerization of allenes in situ: an efficient synthesis of substituted 1,2-dimethylenecyclobutanes with high regio- and stereoselectivities.
abstract: An intermolecular [2+2] cycloaddition reaction for the synthesis of 1,2-dimethylenecyclobutane derivatives from the commercially available starting materials aryl acetylenes, nBuLi, formamides, and trimethylsilyl cyanide (TMSCN) has been achieved. This reaction displays high regio- and stereoselectivities due to the captodative effect. The mechanism of the reaction has been investigated by the deuterium labeling experiments and DFT calculations.
authors.affiliation: Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018 (P.R. China).
authors.forename: Maozhong
authors.initials: M
authors.lastname: Miao
authors.affiliation: Collaborative Innovation Center of Chemistry for Life Sciences, School of Chemistry and Chemical Engineering, Key Laboratory of Mesoscopic Chemistry of MOE, Nanjing University, Nanjing 210093, (P.R. China).
authors.forename: Wenmin
authors.initials: W
authors.lastname: Wang
authors.affiliation: Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018 (P.R. China).
authors.forename: Weijun
authors.initials: W
authors.lastname: Yang
authors.affiliation: Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018 (P.R. China).
authors.forename: Lijun
authors.initials: L
authors.lastname: Xu
authors.affiliation: Collaborative Innovation Center of Chemistry for Life Sciences, School of Chemistry and Chemical Engineering, Key Laboratory of Mesoscopic Chemistry of MOE, Nanjing University, Nanjing 210093, (P.R. China). majing@nju.edu.cn.
authors.forename: Jing
authors.initials: J
authors.lastname: Ma
authors.affiliation: Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018 (P.R. China). renhj@zstu.edu.cn.
authors.forename: Hongjun
authors.initials: H
authors.lastname: Ren
keywords: allenes; cycloaddition; density functional calculations; reaction mechanisms; stereoselectivity