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Volumn 76, Issue 10, 2011, Pages 3664-3675

Calix[4]arenes with two different chemical modifications at the bridges

Author keywords

[No Author keywords available]

Indexed keywords

ARENE DERIVATIVES; CALIX[4]ARENES; CARBONYL GROUPS; PROXIMAL POSITIONS;

EID: 79956122667     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200580m     Document Type: Article
Times cited : (29)

References (43)
  • 8
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    • N1-type reactions have been used for the functionalization of calixarenes at other positions. See
    • N1-type reactions have been used for the functionalization of calixarenes at other positions. See: Troisi, F.; Pierro, T.; Gaeta, C.; Neri, P. Org. Lett. 2009, 11, 697
    • (2009) Org. Lett. , vol.11 , pp. 697
    • Troisi, F.1    Pierro, T.2    Gaeta, C.3    Neri, P.4
  • 14
    • 33748822682 scopus 로고    scopus 로고
    • For a review on the synthesis of calixarenes via the stepwise and fragment condensation methods, see: Böhmer, V. Liebigs Ann./Recueil 1997, 2019
    • (1997) Liebigs Ann./Recueil , pp. 2019
    • Böhmer, V.1
  • 15
    • 77958491684 scopus 로고    scopus 로고
    • For the preparation of calix[4]arenes (with one or three substituted bridges) via reaction of diynes with bis(carbene) complexes
    • For the preparation of calix[4]arenes (with one or three substituted bridges) via reaction of diynes with bis(carbene) complexes, see: Gopalsamuthiram, V.; Huang, R.; Wulff, W. D. Chem. Commun. 2010, 46, 8213
    • (2010) Chem. Commun. , vol.46 , pp. 8213
    • Gopalsamuthiram, V.1    Huang, R.2    Wulff, W.D.3
  • 20
    • 33845591352 scopus 로고    scopus 로고
    • For agostic and methylene hydride complexes of calix[4]arene
    • For agostic and methylene hydride complexes of calix[4]arene, see: Buccella, D.; Parkin, G. J. Am. Chem. Soc. 2006, 128, 16358
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 16358
    • Buccella, D.1    Parkin, G.2
  • 34
    • 79956067041 scopus 로고    scopus 로고
    • note
    • The configuration of the dioxodibromo derivative 4a and its hexabromo precursor 3b was misassigned as cis in ref 2b on the basis of a preliminary crystal structure of 4a (see text).
  • 36
    • 79956075382 scopus 로고    scopus 로고
    • note
    • Three different partial cone conformations are possible for a proximal disubstituted derivative. These forms differ in the identity of the "unique" ring oriented in the opposite direction to the rest. In this paper, when referring to a partial cone conformation, we refer always to the form in which the ring differing in its orientation to the rest is the one connected to the two carbonyl groups.
  • 37
    • 79956142732 scopus 로고    scopus 로고
    • note
    • In an attempt to incoporate amino acid moieties into the bridges, a mixture of 3a, l -glutamic acid and TFE was heated to reflux. No incorporation of the amino acid occurred, but the bis(trifluoroethoxy) derivative 10a was obtained in a higher yield than in the absence of the amino acid. This may be related to the acidic nature of the amino acid. The yield shown in eq 1 (82%) refers to the experiment in the presence of l -glutamic acid.
  • 39
    • 79956124565 scopus 로고    scopus 로고
    • Notably, one of the methoxy groups is oriented "in" (toward the central cavity of the macrocycle) in contrast to the usual "out" conformational preference. "In" conformations of methoxy groups have been observed previously in cases where a methoxy group is intramolecularly hydrogen bonded to a hydroxy group attached at a bridge (ref 13b)
    • Notably, one of the methoxy groups is oriented "in" (toward the central cavity of the macrocycle) in contrast to the usual "out" conformational preference. "In" conformations of methoxy groups have been observed previously in cases where a methoxy group is intramolecularly hydrogen bonded to a hydroxy group attached at a bridge (ref 13b).
  • 40
    • 0346100550 scopus 로고    scopus 로고
    • A trans -dimesityltetrahydroxycalix[4]arene adopts the 1,2-alternate conformation instead of the cone conformation usually adopted by "classical" tetrahydroxycalix[4]arenes since the cone conformation of the dimesityl derivative is destabilized by the presence of one mesityl group in an axial position
    • A trans -dimesityltetrahydroxycalix[4]arene adopts the 1,2-alternate conformation instead of the cone conformation usually adopted by "classical" tetrahydroxycalix[4]arenes since the cone conformation of the dimesityl derivative is destabilized by the presence of one mesityl group in an axial position. Simaan, S.; Biali, S. E. J. Org. Chem. 2004, 69, 95
    • (2004) J. Org. Chem. , vol.69 , pp. 95
    • Simaan, S.1    Biali, S.E.2
  • 41
    • 3743064267 scopus 로고
    • c = π Δ? /?2): Gutowsky, H. S.; Holm, C. H. J. Chem. Phys. 1956, 25, 1228 Since in the case of 18, no coalescence was observed at the highest temperature examined (408 K), the rate calculated by the equation corresponds to a higher limit of the exchange rate at that temperature.
    • (1956) J. Chem. Phys. , vol.25 , pp. 1228
    • Gutowsky, H.S.1    Holm, C.H.2
  • 42
    • 79956081569 scopus 로고    scopus 로고
    • Recently, Wulff and co-workers (ref 12) reported a first example of an optically active methylene-substituted calix[4]arene derivative
    • Recently, Wulff and co-workers (ref 12) reported a first example of an optically active methylene-substituted calix[4]arene derivative.
  • 43
    • 0006576567 scopus 로고
    • For an example of O-Me cleavage at a carbocation in a solvolytic process
    • For an example of O-Me cleavage at a carbocation in a solvolytic process, see: Rappoport, Z.; Greenblatt, J.; Apeloig, Y. J. Org. Chem. 1979, 44, 3687
    • (1979) J. Org. Chem. , vol.44 , pp. 3687
    • Rappoport, Z.1    Greenblatt, J.2    Apeloig, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.