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Volumn , Issue 11, 2008, Pages 1684-1686

Regioselective synthesis of rare 3-halomethylphenols based on formal [3+3] cyclizations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes

Author keywords

Arenes; Cyclization; Regioselectivity; Silyl enol ethers

Indexed keywords

1,3 BIS(TRIMETHYLSILYLOXY) 1,3 BUTADIENE DERIVATIVE; 1,3 BUTADIENE DERIVATIVE; 3 HALOMETHYLPHENOL DERIVATIVE; PHENOL DERIVATIVE;

EID: 48249132859     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1077877     Document Type: Article
Times cited : (9)

References (35)
  • 2
    • 0003907263 scopus 로고
    • Filler, R, Kobayasi, Y, Yagupolskii, L. M, Eds, Elsevier: Amsterdam
    • (b) Fluorine in Bioorganic Chemistry; Filler, R.; Kobayasi, Y.; Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993.
    • (1993) Fluorine in Bioorganic Chemistry
  • 27
    • 33947178424 scopus 로고    scopus 로고
    • For a review of [3+3] cyclizations, see: Feist, H.; Langer, P. Synthesis 2007, 327.
    • For a review of [3+3] cyclizations, see: Feist, H.; Langer, P. Synthesis 2007, 327.
  • 28
    • 0036200130 scopus 로고    scopus 로고
    • For a review of 1,3-bissilyl enol ethers, see
    • For a review of 1,3-bis(silyl enol ethers), see: Langer, P. Synthesis 2002, 441.
    • (2002) Synthesis , pp. 441
    • Langer, P.1
  • 34
    • 48249086824 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of 5a-p To CH 2Cl2 solution (4 mL) of 3a-e (2.0 mmol) and of 4a-i (2.0 mmol) was added TiCl4 (2.0 mmol) at -78 °C under argon atmosphere. The temperature of the solution was allowed to rise to 20 °C during 20 h. The solution was poured into an aq solution of HCl (10, The organic and the aqueous layer were separated and the latter was extracted (3x) with CH2Cl2. The combined organic layers were dried (Na2SO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (SiO2, heptane-EtOAc =10:1, Methyl 6-(Dichlorofluoromethyl)-2-hydroxy-3- methoxybenzoate (5b) Starting with 3a (370 mg, 2.0 mmol, 4b (581 mg, 2.0 mmol, and TiCl4 (380 mg, 2.0 mmol, 5b was isolated as a colorless oil (261 mg, 50, mp 50-51 °C; R f= 0.78 n
    • 35Cl]: 266.01519; found: 266.015398.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.