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Volumn 126, Issue 10, 2004, Pages 3108-3112

Elaboration of Diaryl Ketones into Naphthalenes Fused on Two or Four Sides: A Naphthoannulation Procedure

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CATALYSIS; NAPHTHALENE; OLEFINS;

EID: 1642333104     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038254i     Document Type: Article
Times cited : (110)

References (51)
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    • (b) For evidence that thermal cyclizations of such 1,1-diaryl-2,2-dialkynylethylenes involve the intermediacy of "isobenzenes," see: Hopf, H.; Berger, H.; Zimmermann, G.; Nuchter, U. ; Jones, P. G.; Dix, I. Angew. Chem. 1997, 109, 1236-1239; Angew. Chem., Int. Ed. Engl. 1997, 36, 1187-1190.
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    • (b) For evidence that thermal cyclizations of such 1,1-diaryl-2,2-dialkynylethylenes involve the intermediacy of "isobenzenes," see: Hopf, H.; Berger, H.; Zimmermann, G.; Nuchter, U. ; Jones, P. G.; Dix, I. Angew. Chem. 1997, 109, 1236-1239; Angew. Chem., Int. Ed. Engl. 1997, 36, 1187-1190.
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    • (b) ref 5d, pp 79-81 and references therein.
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    • Reference 5c, Chapter 8
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    • note
    • 2).
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    • note
    • Further evidence for the thiopyrylium ion 7 follows from the similarity of its behavior to that of the oxygen analogue (ref 17).
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    • note
    • 2).
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    • note
    • 3OH to the NMR tube causes the signals for the small amount of pyrylium ion derived from 11 to disappear, and new signals corresponding to those of a methyl ether grow in.
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    • Naphtho[2,1,8,7-klmn]xanthene (14) was first prepared in 1941 from coal tar pitch by Kruber, O. Chem. Ber. 1941, 74, 4B, 1688-1692, but no spectroscopic characterization has subsequently been reported.
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    • Registry No. 203-12-3. Available from Fluka Chemical Co. (catalog no. BCR-139)
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    • note
    • Calculations were performed at the B3LYP/6-31G*//AM1 level of theory, using the Spartan package of programs (Linux v. 02: Wavefunction, Irvine, CA).
  • 44
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    • note
    • A more accurate estimation of relative transition-state geometries would be given by comparisons among the proposed vinylidene intermediates (Scheme 3); however, geometry calculations on transition metal-vinylidene complexes are less reliable, and the trend should be qualitatively no different.
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    • Distance-reactivity relationships of this sort have been noted for other types of cyclization reactions; see, for example: (a) Nicolaou, K. C.; Dai, W. M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416.
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    • Nicolaou, K.C.1    Dai, W.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.