메뉴 건너뛰기




Volumn 71, Issue 4, 2006, Pages 1464-1470

Highly chemoselective methylation and esterification reactions with dimethyl carbonate in the presence of NaY faujasite. The case of mercaptophenols, mercaptobenzoic acids, and carboxylic acids bearing OH substituents

Author keywords

[No Author keywords available]

Indexed keywords

CARBONATES; CARBOXYLIC ACIDS; ESTERS; ORGANIC ACIDS;

EID: 33644513122     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0520792     Document Type: Article
Times cited : (75)

References (71)
  • 16
    • 33644512653 scopus 로고    scopus 로고
    • note
    • Compound 6a was simply isolated by filtration of the zeolite and removal of DMC under vacuum. No further purification was necessary (see Experimental Section).
  • 17
    • 33644499676 scopus 로고    scopus 로고
    • note
    • The FCC purification of compound 12 was made difficult by the presence of some unidentified byproducts (10%) in the reaction mixture. For this reason, a moderate yield of 12 (67% compared to the higher GC amount of 88%) was obtained.
  • 18
    • 33644537284 scopus 로고    scopus 로고
    • note
    • Only compound 13b was further purified by FCC (see Experimental Section).
  • 23
    • 33845471112 scopus 로고
    • +; see Barthomeuf, D. J. Phys. Chem. 1984, 88, 42-45) can promote the formation of compounds 8a,b. The oxidation however apparently stops when dissolved oxygen is consumed.
    • (1984) J. Phys. Chem. , vol.88 , pp. 42-45
    • Barthomeuf, D.1
  • 25
    • 33845471112 scopus 로고
    • +; see Barthomeuf, D. J. Phys. Chem. 1984, 88, 42-45) can promote the formation of compounds 8a,b. The oxidation however apparently stops when dissolved oxygen is consumed.
    • (1984) J. Phys. Chem. , vol.88 , pp. 42-45
    • Barthomeuf, D.1
  • 28
    • 33644510969 scopus 로고    scopus 로고
    • note
    • + and DMC, from 0.14 to 0.86.
  • 29
    • 33644552654 scopus 로고    scopus 로고
    • note
    • Although disulfides 8a,b may also behave as nucleophiles, it seems rather unlikely that they act as intermediates in the formation of the final products 6a,b. In fact, once compounds 8a,b are formed, their amounts remain substantially constant even though S-methyl derivatives 6a,b increase throughout the reaction (entries 3 and 4, Table 1). Moreover, in the reaction of mercaptobenzoic acids 2a,b (Table 2), the corresponding disulfides are never observed.
  • 35
    • 37049087755 scopus 로고
    • It should be noted that in the presence of a base the transesterification of primary alcohols with DMC is a facile reaction: (a) Selva, M.; Trotta, F.; Tundo, P. J. Chem. Soc., Perkin Trans. 2 1992, 4, 519-522.
    • (1992) J. Chem. Soc., Perkin Trans. 2 , vol.4 , pp. 519-522
    • Selva, M.1    Trotta, F.2    Tundo, P.3
  • 53
    • 33644508245 scopus 로고    scopus 로고
    • note
    • Based upon spectroscopic investigations, refs 9 and 11 detail the adsorption pattern of phenols and amines over NaY and NaX faujasites. Since no data are available for carboxylic acids. Scheme 12 is only a reasonable hypothesis. For clarity, the interactions of OH substituents of acids 3-5 with NaY (see Scheme 9) are omitted.
  • 68
  • 70


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.