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Volumn 16, Issue 5, 2010, Pages 1454-1458

Reactive intermediates: A transient electrophilic phosphinidene caught in the act

Author keywords

Carbenes; Cycloaddition; Phosphorus; Tungsten

Indexed keywords

CARBENES; ELECTROSPRAYS; ESI-MS/MS; GAS-PHASE REACTIVITY; IONISATION; LOW-VALENT; ORGANOPHOSPHORUS COMPOUNDS; PHASE DATA; PHOSPHINIDENES; REACTIVE INTERMEDIATE; TANDEM MASS SPECTROMETRY;

EID: 75749157374     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902715     Document Type: Article
Times cited : (27)

References (45)
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    • Eds.: B. M. Trost, F. Malhey, Thieme. Stuttgart
    • a) J. C. Sloolweg, K. Lammertsma in Science of Synthesis Vol. 42 (Eds.: B. M. Trost, F. Malhey), Thieme. Stuttgart. 2009. pp. 15-36;
    • (2009) Science of Synthesis , vol.42 , pp. 15-36
    • Sloolweg, J.C.1    Lammertsma, K.2
  • 6
    • 53049091364 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 3122-3172.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 3122-3172
  • 22
    • 0041432994 scopus 로고    scopus 로고
    • 5W(R)P-N=CMe]; see for example: a) R. Streubel, Top. Curr. Chem. 2003, 223, 91-109;
    • (2003) Top. Curr. Chem. , vol.223 , pp. 91-109
    • Streubel, R.1
  • 27
    • 0038376823 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 2832-2847;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 2832-2847
  • 31
    • 75749108716 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 34
    • 75749141876 scopus 로고    scopus 로고
    • note
    • The ammonium group lowers both the phosphinidene's highest occupied and lowest unoccupied molecular orbitais (HOMO and LUMO) that account for the phosphorus lone pair and empty p orbital, respectively. This makes 3a the more electrophilic species (HOMO 3a: -8.68, 3b: -6.17 eV; LUMO 3a: -6.42, 3b: -3.91 eV).
  • 35
    • 75749115719 scopus 로고    scopus 로고
    • 1J(P,H) = 346 Hz), see reference [7a]
    • 1J(P,H) = 346 Hz), see reference [7a].
  • 36
    • 75749136667 scopus 로고    scopus 로고
    • See for instance the mass spectrometric experiments in reference [8]
    • See for instance the mass spectrometric experiments in reference [8].
  • 37
    • 75749092007 scopus 로고    scopus 로고
    • 5] (M=Mo, W); see reference [7b]
    • 5] (M=Mo, W); see reference [7b].
  • 38
    • 17344362567 scopus 로고    scopus 로고
    • The custom-made 24-pole operates similar to the one described in: L. A. Hammad, G. Gerdes, P. Chen, Organometallics 2005, 24, 1907-1913;
    • (2005) Organometallics , vol.24 , pp. 1907-1913
    • Hammad, L.A.1    Gerdes, G.2    Chen, P.3
  • 39
  • 42
    • 0001033343 scopus 로고
    • 5-complexed phenylphosphirane undergoes [1+2] retroaddition at 150°C (3 h), see: A. Marinetti, C. Charrier, F. Mathey, J. Fischer, Organometallics 1985, 4, 2134-2138, whereas the corresponding diethylamino-substituted phosphirane undergoes [1+2] retroaddition at 70°C (3 h),
    • (1985) Organometallics , vol.4 , pp. 2134-2138
    • Marinetti, A.1    Charrier, C.2    Mathey, F.3    Fischer, J.4
  • 45
    • 75749094536 scopus 로고    scopus 로고
    • Ph.D. Thesis, Vrije Universiteit (Amsterdam)
    • b) J. B. M. Wit, Ph.D. Thesis, Vrije Universiteit (Amsterdam), 2001.
    • (2001)
    • Wit, J.B.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.