Related Experiment Video
Updated: May 19, 2026

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Facile synthesis of dibenzo-7λ3-phosphanorbornadiene derivatives using magnesium anthracene
Alexandra Velian1, Christopher C Cummins
1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.
Abstract:
Unprotected dibenzo-7λ(3)-phosphanorbornadiene derivatives RPA (A = C(14)H(10) or anthracene; R = (t)Bu, dbabh = NA, HMDS = (Me(3)Si)(2)N, (i)Pr(2)N) are synthesized by treatment of the corresponding phosphorus dichloride RPCl(2) with MgA·3THF, in cold THF (~20% to 30% isolated yields). Anthracene and the corresponding cyclic phosphane (RP)(n) form as coproducts. Characteristic NMR features of the RPA derivatives include a doublet near 4 ppm in their (1)H NMR spectra and a triplet peak in the 175-212 ppm region of the (31)P NMR spectrum ((2)J(PH) ~14 Hz). The X-ray structures of the AN-PA and (HMDS)PA derivatives are discussed. Thermolysis of RPA benzene-d(6) solutions leads to anthracene extrusion. This process has a unimolecular kinetic profile for the (i)Pr(2)NPA derivative. The 7-phosphanorbornene anti-(i)Pr(2)NP(C(6)H(8)) could be synthesized (70% isolated yield) by thermolysis of (i)Pr(2)NPA in 1,3-cyclohexadiene.
More Related Videos
Related Concept Videos
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Hydrolysis of Chlorobenzene to Phenol: Dow Process
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

