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Volumn , Issue 14, 2010, Pages 2437-2445

Preparation of dialkyl 1-(Alkylamino)alkylphosphonates, alkyl [1-(Alkylamino)alkyl]phenylphosphinates and [1-(Alkylamino)alkyl] diphenylphosphine oxides via in situ generated iminium ions

Author keywords

aminophosphinates; aminophosphonates; imines; nucleophilic addition; Schiff bases

Indexed keywords

AMINOPHOSPHINATES; AMINOPHOSPHONATES; DIPHENYLPHOSPHINE OXIDES; HIGHER YIELD; HYDROGEN CHLORIDE; IMINIUM IONS; IMINIUM SALTS; IN-SITU; NUCLEOPHILIC ADDITIONS; SCHIFF BASIS;

EID: 77954628569     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218817     Document Type: Article
Times cited : (9)

References (84)
  • 2
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    • This statement is rather intuitive because there is no way to have the imine and the corresponding iminium salts exactly in the same reaction environment. However, experiments in silico indicated that the iminium ions have a lower barrier than the corresponding imines. See for example Tomoda S, Senju T, Kawamura M, Ikeda T, J. Org. Chem. 1999 64 5396
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    • Tomoda, S.1    Senju, T.2    Kawamura, M.3    Ikeda, T.4
  • 7
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    • When our work was finished Metlushka et al. described an addition of trialkyl phosphites into Betti bases in the presence of TFA. We would like to thank a referee for this reference
    • When our work was finished Metlushka et al. described an addition of trialkyl phosphites into Betti bases in the presence of TFA. We would like to thank a referee for this reference:, Metlushka K E., Kashemirov B A., Zheltukhin V F., Sadkova D N., Büchner B, Hess C, Kataeva O N., McKenna C E., Alfonsov V A., Chem. Eur. J. 2009 15 6718
    • (2009) Chem. Eur. J. , vol.15 , pp. 6718
    • Metlushka, K.E.1    Kashemirov, B.A.2    Zheltukhin, V.F.3    Sadkova, D.N.4    Büchner, B.5    Hess, C.6    Kataeva, O.N.7    McKenna, C.E.8    Alfonsov, V.A.9
  • 8
    • 77954642104 scopus 로고    scopus 로고
    • note
    • Searching common databases gives a few hundred publications concerning aminophosphonates, more than three hundred 1-(alkylamino)alkylphosphonates, and about 150 papers describing their synthesis and properties. Since citation of all of them in this short article is inappropriate, we cite here only these papers that are strongly connected to our work. First, general methods of synthesis of these compounds based on the addition of dialkyl phosphonates to alkanimines was described by Pudovik and co-workers and independently by Fields in 1952
  • 9
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    • Chem. Abstr. 1953, 47, 25297
    • Pudovik A N., Dokl. Akad. Nauk SSSR 1952 83 865; Chem. Abstr. 1953, 47, 25297
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    • Pudovik, A.N.1
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    • references cited therein
    • 1H NMR study of dialkyl phosphonates confirmed finally that these compounds exist as non-nucleophilic phosphonate (so-called keto) tautomers, since the presence of nucleophilic dialkyl phosphite tautomers was not found: see Bailey W J., Fox R B., J. Org. Chem. 1963 28 531; and references cited therein
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    • Bailey, W.J.1    Fox, R.B.2
  • 26
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    • references cited therein. The catalytic Kabachnik-Fields reaction was reviewed in this paper
    • Zefirov N S., Matveeva E D., ARKIVOC 2008 (i) 1; and references cited therein. The catalytic Kabachnik-Fields reaction was reviewed in this paper
    • (2008) ARKIVOC , Issue.1 , pp. 1
    • Zefirov, N.S.1    Matveeva, E.D.2
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    • Thai A, Tap Chi Hoa Hoc 1977 15 18; Chem. Abstr. 1979, 90, 152289
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  • 32
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    • note
    • 2] to alkanimines, and described the preparation of eight new alkyl henyl-phosphinates
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    • Chem. Abstr. 1955, 49, 15792
    • Pudovik A N., Dokl. Akad. Nauk SSSR 1953 92 773; Chem. Abstr. 1955, 49, 15792
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  • 46
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    • Chem. Abstr. 1969, 71, 3438
    • [1-(Alkylamino)alkyl]diphenylphosphine oxides were mentioned in the literature, and also in this case, the most frequently employed method was a simple addition of diphenylphosphine oxide to the alkanimines. For examples: see refs. 6h, 14f, and: (a) Pudovik A N., Batyeva E S., Izv. Akad. Nauk SSSR, Ser. Khim. 1968 2391; Chem. Abstr. 1969, 71, 3438
    • (1968) Izv. Akad. Nauk SSSR, Ser. Khim. , pp. 2391
    • Pudovik, A.N.1    Batyeva, E.S.2
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    • Chem. Abstr. 1977, 86, 106726
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  • 84
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    • However, there is a note in the paper published by Sobanov et al., that the reaction between Schiff bases and dialkyl hydrogen phosphonates thoroughly purified from traces of acidic admixtures does not take place:; Chem. Abstr. 2006, 146, 62804
    • However, there is a note in the paper published by Sobanov et al., that the reaction between Schiff bases and dialkyl hydrogen phosphonates thoroughly purified from traces of acidic admixtures does not take place:, Sobanov A A., Zolotukhin A V., Galkina I V., Galkin V I., Cherkasov R A., Russ. J. Gen. Chem. (Engl. Transl.) 2006 76 421; Chem. Abstr. 2006, 146, 62804
    • (2006) Russ. J. Gen. Chem. (Engl. Transl.) , vol.76 , pp. 421
    • Sobanov, A.A.1    Zolotukhin, A.V.2    Galkina, I.V.3    Galkin, V.I.4    Cherkasov, R.A.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.