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Volumn 122, Issue 29, 2000, Pages 6935-6949

A rationally designed prototype of a molecular motor

Author keywords

[No Author keywords available]

Indexed keywords

PHOSGENE;

EID: 0034718057     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001048f     Document Type: Article
Times cited : (214)

References (81)
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    • If the reaction temperature exceeds 5 °C (or if more than 1 equiv of molecular bromine is used), the dibromide 35 is formed in significant amount.
    • If the reaction temperature exceeds 5 °C (or if more than 1 equiv of molecular bromine is used), the dibromide 35 is formed in significant amount.
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    • The benzyne was generated from anthranilic acid with isoamyl nitrite and catalytic trichloroacetic acid (see Experimental Section).47
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    • note
    • (b) Other reaction conditions resulted in varying amounts of undesired brominated products including molecules tentatively characterized as 65 and 66 (see Supporting Information). Br Br MeO-YxWr-5Yx^Br MeOx^Wxs-CHa 65 66
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    • note
    • One of the advantages of designing one's own synthetic target, rather than undertaking the synthesis of a natural product, is that an otherwise extraneous methyl group can always be added to block a side reaction. The disadvantage of designing the target is that, unlike natural products synthesis, it creates a situation of double jeopardy: not only does the synthesis have to succeed, but so must the design; otherwise there is little to show for the effort.
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    • note
    • An example of this type of shielding can be seen not only in the atropisomers themselves, but also by comparing the 'H NMR spectrum of the unwanted photocyclization byproduct 48 with any of the three atropisomers of 6. The spectra of atropisomers 6a, 6b, and 6c all show peaks for triptycene protons upfield of 6.0 ppm. In contrast, the 'H NMR spectrum of 48 shows no peaks for .aromatic protons, triptycene or otherwise, upfield of 7.00 ppm.
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    • note
    • -, the overall reaction is slightly exothermic (AH = -1 kcal/mol)
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    • note
    • Although we discuss the results in terms of a single enantiomer of 6a, strictly speaking, the experiment was actually conducted on racemic material. Since enantiomers in an achiral environment give identical NMR spectra, carrying out the measurement on a single enantiomer would not have increased the information generated by the experiment and, therefore, would not have warranted the investment of effort required to develop a resolution of 6a.
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    • Tlie details of this cell will be published elsewhere.
    • Tlie details of this cell will be published elsewhere.
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    • The composition (contrast Experimental Section regarding preparation of 6) is somewhat solvent-dependent.
    • The composition (contrast Experimental Section regarding preparation of 6) is somewhat solvent-dependent.
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    • For general experimental procedures see the Supporting Information.
    • For general experimental procedures see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.