메뉴 건너뛰기




Volumn 76, Issue 9, 2011, Pages 3576-3581

[3,3]-sigmatropic rearrangement/5-exo-dig cyclization reactions of benzyl alkynyl ethers: Synthesis of substituted 2-indanones and indenes

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLS; BENZYLIC; CYCLIZATION REACTIONS; HIGH YIELD; HORNER-WADSWORTH-EMMONS REACTION; STEP SEQUENCES; TRIFLATES;

EID: 79955565319     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200271s     Document Type: Article
Times cited : (26)

References (33)
  • 1
    • 29244475030 scopus 로고
    • For reviews of the chemistry of ynol ethers and the methods for the synthesis of ynol ethers, see:; In;, Ed.; Marcel Dekker: New York
    • For reviews of the chemistry of ynol ethers and the methods for the synthesis of ynol ethers, see: Brandsma, L.; Bos, H. J.; Arens, J. F. In The Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; pp 751-860.
    • (1969) The Chemistry of Acetylenes , pp. 751-860
    • Brandsma, L.1    Bos, H.J.2    Arens, J.F.3    Viehe, H.G.4
  • 3
    • 0033820360 scopus 로고    scopus 로고
    • Bruckner, D. Synlett 2000, 10, 1402-1404
    • (2000) Synlett , vol.10 , pp. 1402-1404
    • Bruckner, D.1
  • 10
    • 33845279007 scopus 로고
    • For reviews of the Claisen rearrangement, see
    • For reviews of the Claisen rearrangement, see: Ziegler, F. E. Chem. Rev. 1988, 88, 1423
    • (1988) Chem. Rev. , vol.88 , pp. 1423
    • Ziegler, F.E.1
  • 18
    • 0037156378 scopus 로고    scopus 로고
    • The protocol of Muthusamy et al. was followed for diazoketone-alcohol coupling
    • The protocol of Muthusamy et al. was followed for diazoketone-alcohol coupling: Muthusamy, S.; Babu, S. A.; Gunanathan, C. Tetrahedron Lett. 2002, 43, 3133
    • (2002) Tetrahedron Lett. , vol.43 , pp. 3133
    • Muthusamy, S.1    Babu, S.A.2    Gunanathan, C.3
  • 22
    • 0001694036 scopus 로고
    • For seminal papers on substitutent effects on the aliphatic Claisen rearrangment, see
    • For seminal papers on substitutent effects on the aliphatic Claisen rearrangment, see: Burrows, C. J.; Carpenter, B. K. J. Am. Chem. Soc. 1981, 103, 6983
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 6983
    • Burrows, C.J.1    Carpenter, B.K.2
  • 24
    • 78349286235 scopus 로고
    • 0) vs σ for the data for substrates 12a, b, and d shows a break in slope at the data point for 12a, with a strongly negative slope (ρ = -10.5) to 12b and a moderately negative slope (ρ = -1.9) to 12d. The break in slope is suggestive of a change in mechanism upon proceeding from substrates bearing electron-donating substituents (12b) to substrates bearing electron-withdrawing subsituents (12d). See;, See Supporting Information for data graphs.
    • 0) vs σ for the data for substrates 12a, b, and d shows a break in slope at the data point for 12a, with a strongly negative slope (ρ = -10.5) to 12b and a moderately negative slope (ρ = -1.9) to 12d. The break in slope is suggestive of a change in mechanism upon proceeding from substrates bearing electron-donating substituents (12b) to substrates bearing electron-withdrawing subsituents (12d). See Ritchie, C. D.; Sager, W. F. Prog. Phys. Org. Chem. 1964, 2, 323 See Supporting Information for data graphs.
    • (1964) Prog. Phys. Org. Chem. , vol.2 , pp. 323
    • Ritchie, C.D.1    Sager, W.F.2
  • 25
    • 79955554349 scopus 로고    scopus 로고
    • note
    • 0) vs σ for the data for substrates 12a, f, and h shows a break in slope at the data point for 12a, with a negative slope (ρ = -1.62) to 12f and a slightly positive slope (ρ = +0.05) to 12h. Again, the break in slope is suggestive of a change in mechanism upon proceeding from substrates bearing electron-donating substituents (12f) to substrates bearing electron-withdrawing subsituents (12h). See Supporting Information for data graphs.
  • 26
    • 79955564403 scopus 로고    scopus 로고
    • note
    • ato 15d.
  • 27
    • 79955556273 scopus 로고    scopus 로고
    • note
    • 3 as solvent) for 30 minutes, and essentially no change in the isomer ratio was observed. This suggests that the 5- exo-dig cyclization is irreversible under these reaction conditions and that the isomer distributions are under kinetic control.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.