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Volumn 47, Issue 24, 2006, Pages 4001-4005

Chemoselective conversion of aromatic epoxide and 1,2-diol to 1,3-dioxane derivatives with phenyltrimethylammonium tribromide in the presence of a catalytic amount of antimony(III) bromide

Author keywords

1,2 Diol; 1,3 Dioxane; Antimony(III) bromide; Epoxide; Phenyltrimethylammonium tribromide

Indexed keywords

ALKYL PHENYL KETONE; ANTIMONY; BROMINE DERIVATIVE; DIMETHYL SULFOXIDE; DIOXANE DERIVATIVE; EPOXIDE; STILBENE DERIVATIVE;

EID: 33747747071     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.005     Document Type: Article
Times cited : (18)

References (52)
  • 1
  • 39
    • 33747667919 scopus 로고    scopus 로고
    • note
    • 3 in the presence of 1.0 M equiv of benzyltriethylammonium chloride over epoxide 1 in DMSO for 20 h at room temperature. Benzyltriethylammonium chloride was found to promote the oxidation of disubstituted aromatic epoxides and diols to corresponding aldehydes: Sayama, S. Unpublished results.
  • 40
    • 33747681361 scopus 로고    scopus 로고
    • note
    • 3 in the presence of 1,3-propanediol, accompanied by hydrobenzoin (60%). On the contrary, trans-4-chlorostilbene oxide was converted to 2-phenyl-1,3-dioxane 4a (81%) and 2-(4-chlorophenyl)-1,3-dioxane (81%) under the same reaction conditions. Consequently, trans-epoxides were more smoothly oxidized and converted to the corresponding 1,3-dioxanes by this method than cis-epoxides.
  • 41
    • 33747703440 scopus 로고    scopus 로고
    • note
    • For bromoalcohol examples by alternative method, see Ref. 3c.
  • 51
    • 33747668569 scopus 로고    scopus 로고
    • note
    • 3 in DMSO under the same reaction conditions. For the effect of benzyltriethylammonium chloride, see Ref. 9.
  • 52
    • 33747739229 scopus 로고    scopus 로고
    • note
    • 3 (9:1, v/v). 2-Phenyl-1,3-dioxane 4a (79 mg, 0.48 mmol) was obtained in 96% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.