title: Cyclic Amine/Borane Lewis Pairs by the Reaction of N,N-Diallylaniline with Lancaster's H2 B-C6 F5 Reagent.
abstract: Twofold hydroboration of N,N-diallylaniline with the C6 F5 BH2 ⋅SMe2 reagent gave the respective hetero-bicyclo[3.3.0]octane and hetero-methylbicyclo[3.2.0]heptane compounds 4 and 5 as the major products, both showing strong internal N-B amine Lewis base/borane Lewis acid adduct formation. A DFT analysis indicated their formation (and that of a small amount of several isomeric five-membered heterocyclic products) under thermodynamic control. Compound 5 underwent fragmentation with propene liberation to form compound 7 with a formal N=B bond at 100 °C. This product was also obtained from the isomer 4 at much higher temperature (300 °C).
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
authors.forename: Tongdao
authors.initials: T
authors.lastname: Wang
authors.affiliation: Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn, Beringstraße 4, 53115, Bonn, Germany.
authors.forename: Lei
authors.initials: L
authors.lastname: Liu
authors.affiliation: Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn, Beringstraße 4, 53115, Bonn, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Grimme
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
authors.forename: Constantin G
authors.initials: CG
authors.lastname: Daniliuc
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany.
authors.forename: Gerald
authors.initials: G
authors.lastname: Kehr
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149, Münster, Germany. erker@uni-muenster.de.
authors.forename: Gerhard
authors.initials: G
authors.lastname: Erker
keywords: Lewis pairs; hydroboration; thermodynamic control; thermolysis