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Volumn 42, Issue 45, 2003, Pages 5613-5615

Base-Induced Condensation of α-Chloro Oxime Derivatives Furnishes Alkynes

Author keywords

Alkynes; Nitrogen heterocycles; Oximes; Small ring systems

Indexed keywords

CARBON; CONDENSATION; ETHERS; LITHIUM COMPOUNDS; OLEFINS;

EID: 0344667710     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352317     Document Type: Article
Times cited : (18)

References (24)
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    • a) N. de Kimpe in Comprehensive Heterocyclic Chemistry 11, Vol. 1A (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, Oxford, 1996, p. 507;
    • (1996) Comprehensive Heterocyclic Chemistry 11 , vol.1 A , pp. 507
    • De Kimpe, N.1
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    • (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 842
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    • i) W. W. Schoeller, T. Busch, Angew. Chem. 1993, 105, 635; Angew. Chem. Int. Ed. Engl. 1993, 32, 617.
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  • 14
    • 0344788957 scopus 로고    scopus 로고
    • note
    • N2-type displacement of 1a by 2a.
  • 15
    • 0542387374 scopus 로고    scopus 로고
    • For review on 1-azabicyclo[1.1.0]butane, see: R. Bartnik, A. P. Marchand, Synlett 1997, 1029. No studies of this type of 1-azabicyclo[1.1.0]butane with a halo substituent at C2 have been reported to our knowledge.
    • (1997) Synlett , pp. 1029
    • Bartnik, R.1    Marchand, A.P.2
  • 19
    • 0344357113 scopus 로고    scopus 로고
    • note
    • Similar results were obtained when lithium tetramethylpiperidide was used instead of lithium diisopropylamide. The reaction with lithium hexamethyldisilazide yielded 1,4-diphenyl-2-butene-1,4-dione bis(O-methyloxime) as a single product.
  • 23
    • 0345219785 scopus 로고    scopus 로고
    • note
    • The corresponding oxime methanesulfonate and benzoate provided 13ca in yields of 38% and 51%, respectively.
  • 24
    • 0345219786 scopus 로고    scopus 로고
    • note
    • According to the report by House and Berkowitz, the initial stereochemistry of oxime sulfonates is irrelevant in the Neber reaction. However, Maruoka's group has recently reported that the stereochemistry has some effects. They suggested that the generation of azirines from oxime sulfonates with a base favors anti displacement.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.