title: Polar reactions of acyclic conjugated bisallenes.
abstract: The chemical behaviour of various alkyl-substituted, acyclic conjugated bisallenes in reactions involving polar intermediates and/or transition states has been investigated on a broad scale for the first time. The reactions studied include lithiation, reaction of the thus formed organolithium salts with various electrophiles (among others, allyl bromide, DMF and acetone), oxidation to cyclopentenones and epoxides, hydrohalogenation (HCl, HBr addition), halogenation (Br(2) and I(2) addition), and [2 + 2] cycloaddition with chlorosulfonyl isocyanate. The resulting adducts were fully characterized by spectroscopic and analytical methods; they constitute interesting substrates for further organic transformations.
authors: Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106 Braunschweig (Germany), / 391 5388.
authors: Reiner
authors: R
authors: Stamm
authors: Henning
authors: H
authors: Hopf
keywords: conjugated bisallenes; cyclopentenones; epoxidation; halogen addition; hydrohalogenation; ionic additions; metalation; β-lactams
references: Beilstein J Org Chem. 2012;8:1936-98
references: 23209534