title: Stereochemistry of ring-opening/cross metathesis reactions of exo- and endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carbonitriles with allyl alcohol and allyl acetate.
abstract: The ROCM reactions of exo- and endo-2-cyano-7-oxanorbornenes with allyl alcohol or allyl acetate promoted by different ruthenium alkylidene catalysts were studied. The stereochemical outcome of the reactions was established. The issues concerning chemo- (ROCM vs ROMP), regio- (1-2- vs 1-3-product formation), and stereo- (E/Z isomerism) selectivity of reactions under various conditions are discussed. Surprisingly good yields of the ROCM products were obtained under neat conditions.
authors.affiliation: Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland.
authors.forename: Piotr
authors.initials: P
authors.lastname: Wałejko
authors.affiliation: Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland.
authors.forename: Michał
authors.initials: M
authors.lastname: Dąbrowski
authors.affiliation: Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland.
authors.forename: Lech
authors.initials: L
authors.lastname: Szczepaniak
authors.affiliation: Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland.
authors.forename: Jacek W
authors.initials: JW
authors.lastname: Morzycki
authors.affiliation: Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland.
authors.forename: Stanisław
authors.initials: S
authors.lastname: Witkowski
keywords: Grubbs’ catalysts; ROCM; ROMP; Z-selectivity; metathesis