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Indolyne and aryne distortions and nucleophilic regioselectivites.

Abstract:

Density functional theory computations reproduce the surprisingly high regioselectivities in nucleophilic additions and cycloadditions to 4,5-indolynes and the low regioselectivities in the reactions of 5,6-indolynes. Transition-state distortion energies control the regioselectivities, activating the 5 and 6 positions over the 4 and 7 positions, leading to high preferences for 5- and 6-substituted products from 4,5- and 6,7-indolynes, respectively. Orbital and electrostatic interactions have ...

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Publication status:
Published

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Publisher copy:
10.1021/ja9098643

Authors


Cheong, PH More by this author
Bronner, SM More by this author
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Journal:
Journal of the American Chemical Society
Volume:
132
Issue:
4
Pages:
1267-1269
Publication date:
2010-02-05
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
URN:
uuid:51719e09-8298-4bd9-a40b-a933dfae596f
Source identifiers:
117665
Local pid:
pubs:117665

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