A Phosphorus Analogue of p-Quinodimethane with a Planar P4 Ring: A Metal-Free Diphosphorus Source

Rottschäfer D, Neumann B, Stammler H-G, Kishi R, Nakano M, Ghadwal R (2019)
Chemistry 25(13): 3244-3247.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
Para-quinodimethane (pQDM) is a fundamental structural component in many π-conjugated organic molecules and materials. The incorporation of phosphorus atom into π-conjugated frameworks offers unique opportunities for controlling the properties of derived species. A phosphorus analogue of p-quinodimethane (pQDM), (IPrC)2 P4 [5, IPr=C{N(Ar)CH2 }2 ; Ar=2,6-iPr2 C6 H3 ] featuring a planar P4 ring, was readily accessible by KC8 -reduction of (IPrC)(PCl2 )2 (2). Base-mediated C-H functionalization of IPrCH2 (1) with PCl3 afforded 2. The formation of 5 was expected to occur through a dimerization of the transient 3H-diphosphirene (IPrC)P2 (4), which was theoretically suggested to have an intermediate diradical character. Compound 5 underwent photo-induced ring-contraction reaction to form the singlet diradicaloid (IPrCP)2 VI and white phosphorus (P4 ). The formation of and VI and P4 suggested the formal diphosphorus (P2 ) elimination from 5. Indeed, photolysis of a mixture of 1,3-cyclohexadiene (CHD) and 5 led to the formation of P2 -entrapped product (CHD)2 P2 (6). The compound 5 represents the first organophosphorus species that functions as a P2 source.
Erscheinungsjahr
2019
Zeitschriftentitel
Chemistry
Band
25
Ausgabe
13
Seite(n)
3244-3247
ISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/2933681

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Rottschäfer D, Neumann B, Stammler H-G, Kishi R, Nakano M, Ghadwal R. A Phosphorus Analogue of p-Quinodimethane with a Planar P4 Ring: A Metal-Free Diphosphorus Source. Chemistry. 2019;25(13):3244-3247.
Rottschäfer, D., Neumann, B., Stammler, H. - G., Kishi, R., Nakano, M., & Ghadwal, R. (2019). A Phosphorus Analogue of p-Quinodimethane with a Planar P4 Ring: A Metal-Free Diphosphorus Source. Chemistry, 25(13), 3244-3247. doi:10.1002/chem.201805932
Rottschäfer, D., Neumann, B., Stammler, H. - G., Kishi, R., Nakano, M., and Ghadwal, R. (2019). A Phosphorus Analogue of p-Quinodimethane with a Planar P4 Ring: A Metal-Free Diphosphorus Source. Chemistry 25, 3244-3247.
Rottschäfer, D., et al., 2019. A Phosphorus Analogue of p-Quinodimethane with a Planar P4 Ring: A Metal-Free Diphosphorus Source. Chemistry, 25(13), p 3244-3247.
D. Rottschäfer, et al., “A Phosphorus Analogue of p-Quinodimethane with a Planar P4 Ring: A Metal-Free Diphosphorus Source”, Chemistry, vol. 25, 2019, pp. 3244-3247.
Rottschäfer, D., Neumann, B., Stammler, H.-G., Kishi, R., Nakano, M., Ghadwal, R.: A Phosphorus Analogue of p-Quinodimethane with a Planar P4 Ring: A Metal-Free Diphosphorus Source. Chemistry. 25, 3244-3247 (2019).
Rottschäfer, Dennis, Neumann, Beate, Stammler, Hans-Georg, Kishi, Ryohei, Nakano, Masayoshi, and Ghadwal, Rajendra. “A Phosphorus Analogue of p-Quinodimethane with a Planar P4 Ring: A Metal-Free Diphosphorus Source”. Chemistry 25.13 (2019): 3244-3247.
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