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Volumn 62, Issue 42, 2006, Pages 9832-9839

[1,2]-Wittig rearrangement from chloromethyl ethers

Author keywords

1,2 Wittig rearrangement; Chlorine lithium exchange; Chloromethyl ethers; DTBB catalysed lithiation

Indexed keywords

ALCOHOL DERIVATIVE; BENZENE DERIVATIVE; CHLORINE; ETHER DERIVATIVE; LITHIUM;

EID: 33748194144     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.08.028     Document Type: Article
Times cited : (18)

References (86)
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    • An additional problem arises when G=vinyl because the [1,4]-shift of the group R competes with the [1,2]-rearrangement giving an aldehyde. See, for instance:
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    • This type of α-oxygenated organolithium compounds have been used in synthetic organic chemistry by reaction with different carbonyl compounds under Barbier conditions (performing the lithiation in the presence of the electrophile); for a review, see:
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    • We have observed this behaviour in other cases: due to the low density of lithium metal, at 1 mmol scale and with mechanical stirring, a part of the metal remains on the wall of the flask, so an excess (ca. 1:7 molar ratio) should be used, this problem disappearing at higher scale. See, for instance: (Corrigendum: Synthesis 2004, 1720)
    • We have observed this behaviour in other cases: due to the low density of lithium metal, at 1 mmol scale and with mechanical stirring, a part of the metal remains on the wall of the flask, so an excess (ca. 1:7 molar ratio) should be used, this problem disappearing at higher scale. See, for instance:. Yus M., Moreno B., and Foubelo F. Synthesis (2004) 1115-1118 (Corrigendum: Synthesis 2004, 1720)
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    • note
    • Compound 1n was thermically very unstable and was obtained after distillation in ca. 70% purity, containing ca. 30% of benzyl chloride. This mixture was used directly for the lithiation step, the corresponding given yield for the product 2n (Table 1, entry 14) being based on the mentioned proportion of compound 1n.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.