Reactivity of an Intramolecular Fluorophosphonium Fluoroborate

The reactions of the intramolecular frustrated Lewis pair‐adduct Ph2PC(p‐Tol)C(C6F5)B(C6F5)2(CNtBu) with XeF2 gave Ph2P(F)C(p‐Tol)C(C6F5)B(F)(C6F5)2 (3). This species reacts with two equivalents of Al(C6F5)3⋅C7H8 producing the salt, [Ph2P(F)C(p‐Tol)C(C6F5)B(C6F5)2][F(Al(C6F5)3)2] (4), whereas rea...

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Bibliographic Details
Published in:Chemistry : a European journal 2014-09, Vol.20 (36), p.11287-11290
Main Authors: Ekkert, Olga, Caputo, Christopher B., Pranckevicius, Conor, Daniliuc, Constantin G., Kehr, Gerald, Erker, Gerhard, Stephan, Douglas W.
Format: Article
Language:English
Subjects:
aromatization
Cationic
Chemistry
Derivatives
Equivalence
fluorophosphonium cations
frustrated Lewis pairs
Oxidation
photochemistry
Photolysis
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Summary:The reactions of the intramolecular frustrated Lewis pair‐adduct Ph2PC(p‐Tol)C(C6F5)B(C6F5)2(CNtBu) with XeF2 gave Ph2P(F)C(p‐Tol)C(C6F5)B(F)(C6F5)2 (3). This species reacts with two equivalents of Al(C6F5)3⋅C7H8 producing the salt, [Ph2P(F)C(p‐Tol)C(C6F5)B(C6F5)2][F(Al(C6F5)3)2] (4), whereas reaction with HSiEt3/B(C6F5)3 gave Ph2P(F)C(p‐Tol)C(H)B(C6F5)3 (5). The photolysis of 3 resulted in aromatization affording the phenanthralene derivative Ph2P(F)C(p‐Tol(o‐C6F4))CB(F)(C6F5)2 (6). Frustrated reactions! Oxidation of the intramolecular frustrated Lewis pair Ph2PC(p‐Tol)C(C6F5)B(C6F5)2(CNtBu) with XeF2 gave the corresponding phosphonium fluoroborate, which reacts with Al(C6F5)3⋅C7H8 and HSiEt3/B(C6F5)3 to give cationic and B(C6F5)3 derivatives, respectively. Photolysis of the phosphonium fluoroborate resulted in aromatization affording the phenanthralene derivative Ph2P(F)C(p‐Tol(o‐C6F4))CB(F)(C6F5)2.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201403110