title: X-ray structures of cyclophanes derived from naphtho[1,2-c:5,6-c]difuran and the synthesis, structure, and reaction kinetics of its 1,3,6,8-tetrasilylated derivative.
abstract: A silylated derivative of naphtho[1,2-c:5,6-c]difuran, 1,3,6,8-tetrakis(tert-butyldimethylsilyl)naphtho[1,2-c:5,6-c]difuran, has been isolated and its X-ray crystal structure determined. Bond localization confirms the polyene character of this isobenzofuran ring system. This molecule undergoes two successive Diels-Alder reactions with second-order rate constants differing by over 2 orders of magnitude, consistent with predictions based on their structure-count ratios and with the reactivity of the novel 1,3-bis(tert-butyldimethylsilyl)isobenzofuran. Crystal structures of two cyclophanes derived from the reaction of naphtho[1,2-c:5,6-c]difuran and bis(imide) or bis(ester) dienophiles show marked differences in the conformation of the aliphatic chain found in the solid state.
authors.affiliation: Department of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, AB T1K 3M4, Canada.
authors.forename: Steven J
authors.initials: SJ
authors.lastname: Robbins
authors.forename: Michelle E
authors.initials: ME
authors.lastname: Thibault
authors.forename: Jason D
authors.initials: JD
authors.lastname: Masuda
authors.forename: David R
authors.initials: DR
authors.lastname: Ward
authors.forename: René T
authors.initials: RT
authors.lastname: Boeré
authors.forename: Peter W
authors.initials: PW
authors.lastname: Dibble