title: Dialkylaluminum hydride-promoted cyclodimerization of silylated 1,3-enynes via skeletal rearrangement.
abstract: The dialkylaluminum hydride-promoted reaction of 1-silylalk-3-en-1-ynes gave symmetrical 1,2,3,5-tetrasubstituted benzenes as single regioisomers. The novel cyclodimerization via skeletal rearrangement can be rationalized by an unprecedented mechanism involving sequential hydroalumination, alkene isomerization, carboalumination, carbon-carbon bond cleavage, and retro-hydroalumination.
authors: Department of Applied Chemistry, Graduate School of Science and Engineering, Saitma University, 255 Shimo-ohkubo, Sakura-ku, Saitama 338-8570, Japan.
authors: Hidenori
authors: H
authors: Kinoshita
authors: Tomoyuki
authors: T
authors: Ishikawa
authors: Katsukiyo
authors: K
authors: Miura
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D000535:Aluminum / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000480:Alkynes; D001555:Benzene Derivatives; D009942:Organometallic Compounds; D012821:Silanes; D000535:Aluminum