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Tetrahedron Letters
Volumn 32, Issue 9, 1991, Pages 1209-1212
Regioselective dehydration in cyclic system with triphenylphosphine-azodicarboxylate
Author keywords

[No Author keywords available]
Indexed keywords

CYCLOHEXANE DERIVATIVE;
EID: 0026073167     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)92046-X     Document Type: Article
Times cited : (10)
References (21)
  • 4
    • 84918598002 scopus 로고    scopus 로고
    • The term “Saytzeff” expresses more substituted olefin and “Hoffmann”, less substituted one in this paper.
  • 10
    • 84918639715 scopus 로고    scopus 로고
    • 1H NMR integration 2: 5.09 (1H), 5.4 (0.60/2H). 3: 5.38 (1H), 5.6 (0.10/2H). 4: 5.38 (1H), 5.43 and 5.65 (0.06/2H). 5: 5.37 (1H), 5.8 (0.11/2H). 6: 5.37 (1H), 5.53 and 5.64 (0.04/2H).
  • 11
    • 85077634689 scopus 로고
    • The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products
    • (1981) Synthesis , pp. 1
    • Mitsunobu1
  • 12
    • 0000600383 scopus 로고
    • 2 is presumed to be formed at the initial stage, oxo-phosphonium salt should be a reactive intermediate in the present elimination reaction:, and references therein.
    • (1989) J. Org. Chem. , vol.54 , pp. 3045
    • Camp1    Jenkisn2
  • 13
    • 84918650513 scopus 로고    scopus 로고
    • In 1c, when a ring-flipped conformation is taken into consideration in the transition state (cf. conformer A or B), the two eliminating groups should be in the same trans diaxial relationship as that in 1b.
  • 15
    • 37049047517 scopus 로고
    • 801. Mechanism of elimination reactions. Part XXII. Anomalous elimination from the trimethylneomenthylammonium ion
    • Saytzeff selectivity of the elimination of trimethylethylneomethylammonium ion was explained by steric pressure:
    • (1960) Journal of the Chemical Society (Resumed) , pp. 4094
    • Hughes1    Wilby2
  • 16
    • 0006195685 scopus 로고
    • As we were interested in differences of selectivity between equatorial and axial alcohols, we used tert-butylcyclohexanols as substrates. Alcohol 3 was prepared according to the literature:
    • (1969) J. Org. Chem. , vol.34 , pp. 3070
    • Huff1    Tuller2    Caine3
  • 18
    • 33847088162 scopus 로고
    • 3) 5: 0.90 (d, J =7Hz, 3H, Me), 3.72 (dt, J =11, 5Hz, 1H, CH OH). 6: 0.95 (d, J =6Hz, 3H, Me), 3.87 (br s, 1H, CH OH).
    • (1977) J. Org. Chem. , vol.42 , pp. 183
    • House1    Lusch2
  • 19
    • 84918616720 scopus 로고    scopus 로고
    • A cyclic syn-elimination may also be considered. However, this possibility can be eliminated since the present reactions take place quite smoothly at room temperature although pyrolytic conditions are usually required for this type of reaction. Moreover, opposite regioselectivity obtained by the elimination of 1a and 1c can not be explained by the syn-elimination mechanism.
  • 20
    • 84918613907 scopus 로고    scopus 로고
    • The program MacroModel was employed for this calculation: Still, W. C.; Mohamadi, F.; Richard, N. G. L.; Guida, W. C.; Lipton, M.; Liskamp, R.; Chang, G.; Hendrickson, T.; Degunst, F.; Hasel, W. MacroModel V 2.5, Department of Chemistry, Columbia University, New York, NY 10027.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.