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Volumn , Issue 17, 2008, Pages 2708-2710

Regioselective synthesis of 2-(arylthio)benzoates by the first catalytic [3+3] cyclocondensations of 3-(arylthio)-1-(trimethylsilyloxy)-1,3-butadienes with 1,1,3,3-tetramethoxypropane

Author keywords

Arenes; Cyclizations; Diaryl sulfides; Regioselectivity; Silyl enol ethers

Indexed keywords

1,1,3,3 TETRAMETHOXYPROPANE; 1,3 BUTADIENE DERIVATIVE; 2 PHENYLTHIOBENZOATE; 3 (PHENYLTHIO) 1 (SILYLOXY) 1,3 BUTADIENE; BENZOIC ACID DERIVATIVE; METHYL 2 PHENYLTHIOBENZOATE; PROPANE; UNCLASSIFIED DRUG;

EID: 55449114763     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083516     Document Type: Article
Times cited : (5)

References (35)
  • 11
    • 0025140829 scopus 로고
    • For the trifluoromethanesulfonic acid catalyzed sulfurization of cycloalkanes, see
    • (c) For the trifluoromethanesulfonic acid catalyzed sulfurization of cycloalkanes, see: Olah, G. A.; Wang, Q.; Prakash, G. K. S. J. Am. Chem. Soc. 1990, 112, 3697.
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 3697
    • Olah, G.A.1    Wang, Q.2    Prakash, G.K.S.3
  • 26
    • 33947178424 scopus 로고    scopus 로고
    • For a review on [3+3] cyclizations, see: Feist, H.; Langer, P. Synthesis 2007, 327.
    • For a review on [3+3] cyclizations, see: Feist, H.; Langer, P. Synthesis 2007, 327.
  • 27
    • 0036200130 scopus 로고    scopus 로고
    • For a review on 1,3-bis(silyloxy)-1,3-butadienes, see
    • For a review on 1,3-bis(silyloxy)-1,3-butadienes, see: Langer, P. Synthesis 2002, 441.
    • (2002) Synthesis , pp. 441
    • Langer, P.1
  • 35
    • 55449092454 scopus 로고    scopus 로고
    • Typical Experimental Procedure To a CH2Cl2 solution (2 mL/mmol of 3) of 3 (1.5 mmol) and of 1,1,3,3-tetramethoxypropane (1.0 mmol) was added TMSOTf(0.1 mmol) at -78 °C. The solution was allowed to warm to 20 °C within 20 h. To the solution was added a diluted aq solution of HCl (15 mL, The organic and the aqueous layer were separated, and the latter was extracted with CH2Cl2 (3 × 15 mL, The combined organic layers were dried (Na2SO 4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by chromatography. Methyl 2-(Phenylthio)benzoate (5a) Starting with 1,1,3,3-tetramethoxypropane (0.33 mL, 2.0 mmol, 3a (843 mg, 3.0 mmol, TMSOTf (0.036 mL, 0.2 mmol, and CH2Cl2 (4 mL, 5a was isolated as a highly viscous colourless oil (275 mg, 53, 1H NMR (250 MHz, CDCl3, δ, 3.66 s, 3 H, OCH 3
    • +]: 244.05525; found: 244.05570.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.