Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 34, Pages 13966-13969Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja306723r
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Funding
- NIH-NIGMS [R01 GM090007]
- Boehringer Ingelheim
- DuPont
- Eli Lilly
- Amgen
- AstraZeneca
- Foote Fellowship
- Stauffer Charitable Trust
- University of California, Los Angeles
- National Science Foundation [CHE-0548209, CHE-1048804]
- National Center for Research Resources [S10RR025631]
- Direct For Mathematical & Physical Scien [1048804, 1059084] Funding Source: National Science Foundation
- Division Of Chemistry [1048804, 1059084] Funding Source: National Science Foundation
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We report an experimental and computational study of 3-silylarynes. The addition of nucleophiles yield ortho-substituted products as a result of aryne distortion, but meta-substituted products form predominately when the nucleophile is large. Computations correctly predict the preferred site of attack observed in both nucleophilic addition and cycloaddition experiments. Nucleophilic additions to 3-tert-butylbenzyne, which is not significantly distorted, give meta-substituted products.
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