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Volumn 68, Issue 22, 2003, Pages 8711-8714

Unexpected Single-Step Formation of 1,2-anti-Heterodisubstituted Calix[4]arenes upon Alkylation of a Tribenzoyl Precursor

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR STRUCTURE; SUBSTITUTION REACTIONS;

EID: 0142258943     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035150h     Document Type: Article
Times cited : (10)

References (41)
  • 1
    • 0004146786 scopus 로고
    • The Royal Society of Chemistry: Cambridge
    • (a) Gutsche, C. D. Calixarenes; The Royal Society of Chemistry: Cambridge, 1989.
    • (1989) Calixarenes
    • Gutsche, C.D.1
  • 3
    • 0004268367 scopus 로고    scopus 로고
    • The Royal Society of Chemistry: Cambridge
    • (c) Gutsche, C. D. Calixarenes Revisited; The Royal Society of Chemistry: Cambridge, 1998.
    • (1998) Calixarenes Revisited
    • Gutsche, C.D.1
  • 4
    • 0004266535 scopus 로고    scopus 로고
    • Mandolini, L., Ungaro, R., Eds.; Imperial College Press: London, and references therein
    • (d) Calixarenes in Action; Mandolini, L., Ungaro, R., Eds.; Imperial College Press: London, 2000 and references therein.
    • (2000) Calixarenes in Action
  • 31
    • 0001355225 scopus 로고
    • Only two examples of hetero-1,2-dialkylation are known, though these compounds were obtained after several steps involving protection/ deprotection sequences: (a) Iwamoto, K.; Shimizu, H.; Araki, K.; Shinkai, S. J. Am. Chem. Soc. 1993, 115, 3997-4006.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 3997-4006
    • Iwamoto, K.1    Shimizu, H.2    Araki, K.3    Shinkai, S.4
  • 33
    • 0041616339 scopus 로고
    • Chawla, H. M.; Pathak, M. Bull. Soc. Chim. Fr. 1991, 128, 232-243. A partial cone isomer was suggested as the major product on the basis of the NMR spectrum.
    • (1991) Bull. Soc. Chim. Fr. , vol.128 , pp. 232-243
    • Chawla, H.M.1    Pathak, M.2
  • 34
    • 0142174495 scopus 로고    scopus 로고
    • note
    • In our hands, at 1 M calixarene concentration (Chawla's conditions), a mixture of the symmetrical partial cone isomer 2 (49%), the asymmetric partial cone isomer 3 (26%), and the cone isomer (25%) in an 83% isolated yield was obtained.
  • 38
    • 0142174496 scopus 로고    scopus 로고
    • note
    • Compound 8 was actually isolated as a mixture of a 1,3-alternate and a partial cone isomer, which could not be separated by crystallization or column chromatography.
  • 39
    • 0035969007 scopus 로고    scopus 로고
    • A 1,2-proximal dibenzoyl calix[4]arene has been reported: Dospil, G.; Schatz, J. Tetrahedron Lett. 2001, 42, 7837-7840. However, in these studies the syn conformer was employed.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 7837-7840
    • Dospil, G.1    Schatz, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.