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Volumn 30, Issue 42, 1989, Pages 5747-5750

Allene synthesis from 2-alkyn-1-ols

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EID: 0000323463     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)76187-9     Document Type: Article
Times cited : (22)

References (21)
  • 1
    • 84918628818 scopus 로고    scopus 로고
    • Myers, A.G.; Kuo, E.Y.; Finney, N.S., submitted for publication in J. Am. Chem. Soc.
  • 5
  • 7
    • 0000919890 scopus 로고
    • Similarly, Wolff-Kishner reduction of α,β-unsaturated carbonyl compounds often leads to olefin transposition, see
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 7016
    • Corey1    Cane2    Libit3
  • 8
    • 84918647363 scopus 로고
    • In Reduction, R.L. Augustine, Marcel Dekker, New York
    • (1968) , pp. 182
    • Reusch1
  • 10
    • 84932438959 scopus 로고
    • Umsetzung 1,1-disubstituierter Hydrazine mit Azodicarbonsäure-diethylester
    • For the oxidation of 1,1- and 1,2-dialkylhydrazines, respectively, with diethyl azodicarboxylate, see
    • (1980) Liebigs Annalen der Chemie , pp. 219
    • Fahr1    Koch2
  • 12
    • 0002444147 scopus 로고
    • Photolysis of the azo-precursors of 2,3- and 1,8-naphtoquinodimethane. Preliminary communication
    • (1976) Helvetica Chimica Acta , vol.59 , pp. 2273
    • Gisin1    Wirz2
  • 13
    • 84918609163 scopus 로고    scopus 로고
    • Use of an acetylenic precursor for the allene functional group allows stereospecific formation of the vinylallene linkage (see reference 1), satisfying one of the criteria set forth above.
  • 14
    • 84918618154 scopus 로고    scopus 로고
    • Oxidation with the less expensive DEAD typically produced small amounts (≤ 5%) of products of carboethoxy transfer to the hydrazine. Oxidation with MTAD was more rapid and could be carried out at lower temperature (−78 °C). Yields with each reagent were roughly comparable and both led to complete reaction within 5 min at 0 °C.
  • 15
    • 0001641492 scopus 로고
    • Alcohol 8 was synthesized as follows: Reaction of cyclohexene oxide with the 1:1 complex of boron trifluoride etherate and the lithiated tetrahydropyranyl ether of propargyl alcohol in tetrahydrofuran at −78 °C produced the trans-cyclohexanol in 82% yield
    • (1983) Tetrahedron Lett. , vol.24 , pp. 391
    • Yamaguchi1    Hirao2
  • 16
    • 45549118868 scopus 로고
    • Silylation with t-butyldimethylsilyl chloride-4-dimethylaminopyridine-triethylamine and selective removal of the tetrahydropyranyl protecting group with hydrogen peroxide-trichloroacetic acid in t-butyl alcohol-methylene chloride, then furnished alcohol 8 in 70% yield for the two steps. Other methods for removal of the tetrahydropyranyl protecting group induced competitive desilylation.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 5609
    • Myers1    Fundy2    Lindstrom3
  • 17
    • 84918597825 scopus 로고    scopus 로고
    • Unlike substrate 3, alcohol 7 underwent clean desilylation when subjected to conditions leading to allene formation.
  • 19
    • 84918620890 scopus 로고    scopus 로고
    • Estimates of the maximum rotation of (S)-11 are in the range −197.7 to −237±23°. For discussion, see reference 11.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.