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Volumn 72, Issue 16, 2007, Pages 6006-6015

Nucleophilic substitution reactions of alcohols with use of montmorillonite catalysts as solid Brønsted acids

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; ANILINE; BYPRODUCTS; CATALYSTS; CLAY MINERALS; NUCLEOPHILES; SUBSTITUTION REACTIONS;

EID: 34547613570     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070416w     Document Type: Article
Times cited : (213)

References (79)
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    • The strength of the Al3+-mont was determined by the method of Niwa and Katada, see ref 9
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    • During preparation of this manuscript, substitution of benzylic alcohols with only p-niroaniline was reported, see refs 2b and 3d.
    • During preparation of this manuscript, substitution of benzylic alcohols with only p-niroaniline was reported, see refs 2b and 3d.
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    • After reaction of 2a with 1a under the reaction conditions of Table 1, entry 1 (88% combined yield, N:ortho:para adducts = 86:10:4), further treatment of the reaction mixture at 150°C for 24 h afforded a 59% yield of the ortho adduct as a major product (75% combined yield, N:ortho:para = 9:79:12).
    • After reaction of 2a with 1a under the reaction conditions of Table 1, entry 1 (88% combined yield, N:ortho:para adducts = 86:10:4), further treatment of the reaction mixture at 150°C for 24 h afforded a 59% yield of the ortho adduct as a major product (75% combined yield, N:ortho:para = 9:79:12).
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    • Allylation of 1,3-dicarbonyls with allyl alcohols is usually catalyzed by Pd catalysts, see ref 13.
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    • Reaction time was not reported
    • Reaction time was not reported.
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    • a value of protonated aniline (3.6) is much lower than that of aniline (30.6); see: Fu, Y.; Li, R.-Q.; Liu, R.; Guo, Q.-X. J. Am. Chem. Soc. 2004, 126, 814.
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    • In the reaction of neutral nitrogen nucleophile of amides, this deactivation of H+ site might not occur
    • + site might not occur.
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    • 2/g]).
    • 2/g]).
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    • The H-mont-catalyzed reaction of 8a with ether 10b from the secondary alcohol of 2g afforded quantitative yield of the α-benzhydryl acetylacetone.
    • The H-mont-catalyzed reaction of 8a with ether 10b from the secondary alcohol of 2g afforded quantitative yield of the α-benzhydryl acetylacetone.
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    • Formation of triisopropylsilanol was detected by GC-MS analysis together with 12a in the reaction of 2g and triisopropylallylsilane.
    • Formation of triisopropylsilanol was detected by GC-MS analysis together with 12a in the reaction of 2g and triisopropylallylsilane.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.