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Volumn 47, Issue 27, 2008, Pages 5067-5070

Decoupling deprotonation from metalation: Thia-fries rearrangement

Author keywords

Basicity; Metalation; Migration; Rearrangements; Superbases

Indexed keywords

BASICITY; METALATION; MIGRATION; REARRANGEMENTS; SUPERBASES;

EID: 49849097111     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800750     Document Type: Article
Times cited : (64)

References (67)
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    • 3, of which about 86% are triflones (n=0).
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    • Rearrangement is highly dependent on the purity of the BuLi used to prepare LDA: the presence of LiX accelerates benzyne generation
    • Rearrangement is highly dependent on the purity of the BuLi used to prepare LDA: the presence of LiX accelerates benzyne generation.
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    • 2H]-p-1 is recovered in high isotopic purity.
    • 2H]-p-1 is recovered in high isotopic purity.
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    • For leading references, see
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    • 2 (P. G. Williard, G. B. Carpenter, J. Am. Chem. Soc. 1986, 108, 462-468) in THF, undergoing instead a slow triflate displacement (SNAr or SRAr).
    • 2 (P. G. Williard, G. B. Carpenter, J. Am. Chem. Soc. 1986, 108, 462-468) in THF, undergoing instead a slow triflate displacement (SNAr or SRAr).
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    • References [45-47] cited in reference [9d
    • b) References [45-47] cited in reference [9d].
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    • [o-Ar(OTf)Pd] species do not (rapidly) eliminate: a) T. Kamikawa, T. Hayashi, Tetrahedron Lett. 1997, 38, 7087-7090;
    • [o-Ar(OTf)Pd] species do not (rapidly) eliminate: a) T. Kamikawa, T. Hayashi, Tetrahedron Lett. 1997, 38, 7087-7090;
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    • ortho-TMS aryl triflates generate arynes, without thia-Fries rearrangement, for example: E. Yoshikawa, K. V. Radhakrishnan, Y. Yamamoto, Tetrahedron Lett. 2000, 41, 729-731.
    • ortho-TMS aryl triflates generate arynes, without thia-Fries rearrangement, for example: E. Yoshikawa, K. V. Radhakrishnan, Y. Yamamoto, Tetrahedron Lett. 2000, 41, 729-731.
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    • All calculations were carried out by using the Jaguar 4.0 program package (Schrodinger, Inc., Portland, Oregon, 2000); see the Supporting Information for full computational details.
    • All calculations were carried out by using the Jaguar 4.0 program package (Schrodinger, Inc., Portland, Oregon, 2000); see the Supporting Information for full computational details.
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    • This process would require generation of catalytic quantities of o-(CF3SO2)-C6H3Cl-OSO 2CF3 as a chain propagating agent
    • 3 as a chain propagating agent.
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    • Account: Y. Kondo, M. Ueno, Y. Tanaka, J. Synth. Org. Chem. Jpn. 2005, 63, 453-463.
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    • 4H)(OH)] appears to cause hydrolysis of the triflate group and, on occasion, diaryl ether side products, presumably arising from aryne capture by the phenolate, were also detected (mass spectrometry).
    • 4H)(OH)] appears to cause hydrolysis of the triflate group and, on occasion, diaryl ether side products, presumably arising from aryne capture by the phenolate, were also detected (mass spectrometry).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.