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- Title
Formation of Active Cyclic Five‐membered Frustrated Phosphane/Borane Lewis Pairs and their Cycloaddition Reactions.
- Authors
Dong, Shunxi; Daniliuc, Constantin G.; Kehr, Gerald; Erker, Gerhard
- Abstract
The cyclic five‐membered frustrated phosphane/borane Lewis pairs 11 a, b featuring the bulky octaethylhydrindacenyl‐ (Eind) substituent or its mono‐bromo derivative (BrEind) at phosphorus are monomeric at room temperature. The reactive frustrated Lewis pairs (FLPs) cleave dihydrogen. The cyclic FLP 11 b (BrEind) undergoes 1,2‐P/B addition to ethylene to give the zwitterionic heteronorbornane derivative 14 b. It reacts similarly with the carbon–carbon double bond of norbornene. With a variety of organic π‐reagents, the cyclic FLP 11 b often undergoes reaction sequences reminiscent of the Alder–Rickert reaction: the cycloaddition reaction is followed by rapid cycloreversion to form new five‐membered heterocyclic FLP products with extrusion of ethene. Reactions of 11 b with benzaldehyde or with acetylenes follow this reaction pattern.
- Subjects
LEWIS pairs (Chemistry); RING formation (Chemistry); BORANES; CARBON-carbon bonds; DOUBLE bonds; DEHYDROGENATION
- Publication
Chemistry - A European Journal, 2020, Vol 26, Issue 3, p745
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201904919