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Volumn 62, Issue 25, 2006, Pages 5986-5994

A free radical Mannich type reaction: selective α-CH aminomethylation of ethers by Ti(III)/t-BuOOH system under aqueous acidic conditions

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; ETHER DERIVATIVE; HYDROGEN; METHYLENE IMINIUM SALT; SODIUM CHLORIDE; TERT BUTYL HYDROPEROXIDE; TITANIUM; UNCLASSIFIED DRUG;

EID: 33747342194     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.04.014     Document Type: Article
Times cited : (39)

References (68)
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    • For reviews on radical addition to C{double bond, long}N bonds see:
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    • Formaldehyde-imines have never been isolated since they rapidly trimerise to s-triazines and formaldiminium ions react with water even at room temperature.
  • 45
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    • Addition of α-alkoxyalkyl radicals to C{double bond, long}N double bonds:
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    • note
    • When 1,4-dioxane was used, acetic acid was not added.
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    • The PMP protecting group can be readily removed upon CAN oxidative transformation.
    • The PMP protecting group can be readily removed upon CAN oxidative transformation. Hasegawa M., Tanijama D., and Tomioka K. Tetrahedron 56 (2000) 10153-10158
    • (2000) Tetrahedron , vol.56 , pp. 10153-10158
    • Hasegawa, M.1    Tanijama, D.2    Tomioka, K.3
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    • 33747375056 scopus 로고    scopus 로고
    • note
    • Only one of the possible intermediates involved in the formation of A has been reported for simplicity (see Ref. 1).
  • 55
    • 33747338246 scopus 로고    scopus 로고
    • -1) and the addition to iminium salts is significantly more favourable for enthalpic reasons.
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    • In the condensation of aniline with aromatic aldehydes, electron-donor p-substituents on the aldehyde decrease the rate of imine formation. A satisfactory Hammet correlation was observed:
    • In the condensation of aniline with aromatic aldehydes, electron-donor p-substituents on the aldehyde decrease the rate of imine formation. A satisfactory Hammet correlation was observed:. Pratt E.F., and Kamlet M.J. J. Org. Chem. 26 (1961) 4029-4031
    • (1961) J. Org. Chem. , vol.26 , pp. 4029-4031
    • Pratt, E.F.1    Kamlet, M.J.2
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    • 33747351251 scopus 로고    scopus 로고
    • For the synthesis of N-aliphatic aminoethers see:
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    • Merck Co. Inc. U.S. Patent 2,155,446, 1937;
  • 64
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    • Ciba Pharm. Prod. Inc. U.S. Patent 2,903,464, 1956;. Chem. Abstr. (1960) 2371
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    • N-aromatic 1,2-aminoethers (in particular 3l) belong to a new class of ethylene-1-octene copolymerisation catalysts, which are obtained starting from 1,2-aminoethers and aryl bromide using Pd-catalysed chemistry at high temperature.
    • N-aromatic 1,2-aminoethers (in particular 3l) belong to a new class of ethylene-1-octene copolymerisation catalysts, which are obtained starting from 1,2-aminoethers and aryl bromide using Pd-catalysed chemistry at high temperature. Boussie T.R., Diamond G.M., Goh C., Hall K.A., LaPointe A.M., Leclerc M., Lund C., Murphy V., Shoemaker J.A.W., Tracht U., Turner H., Zhang J., Uno T., Rosen R.K., and Stevens J.C. J. Am. Chem. Soc. 125 (2003) 4306-4317
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 4306-4317
    • Boussie, T.R.1    Diamond, G.M.2    Goh, C.3    Hall, K.A.4    LaPointe, A.M.5    Leclerc, M.6    Lund, C.7    Murphy, V.8    Shoemaker, J.A.W.9    Tracht, U.10    Turner, H.11    Zhang, J.12    Uno, T.13    Rosen, R.K.14    Stevens, J.C.15
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    • See Ref. 20d.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.