2001年11月
First isolation of monomeric N-alkoxyarylaminyl radicals and their chemical and magnetic properties
JOURNAL OF ORGANIC CHEMISTRY
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- 巻
- 66
- 号
- 22
- 開始ページ
- 7456
- 終了ページ
- 7463
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1021/jo0106288
- 出版者・発行元
- AMER CHEMICAL SOC
The present report describes the first isolation of monomeric N-alkoxyarylaminyls and their chemical and magnetic properties. Reaction of the corresponding lithium amides of 2,4-diaryl-6-tert-butylanilines, 2,6-diaryl-4-tert-butylanilines, or 2,4,6-triarylanilines with tert-butyl peroxybenzoate in THF at -78 degreesC yielded quite persistent N-tert-butoxy-2,4-diaryl-6-tert-butylphenylaminyls (1), N-tert-butoxy-2,6-diaryl-4-tert-butylphenylaminyls (2), and N-tert-butoxy-2,4,6-triarylphenylaminyls (3), respectively, which were isolated in the monomeric form in 17-25% yields. All radicals prepared were oxygen insensitive and thermally very stable. X-ray crystallographic analyses were carried out for two radicals, and it was shown that the N and O atoms are coplanar with the anilino benzene ring. The ESR spectra of 1-3 gave alpha (N) = 0.984-1.05 and alpha (H) (anilino meta) = 0.158-0.170 mT (g = 2.0041-2.0043), indicating that the unpaired electron mainly resides on the nitrogen and anilino benzene ring. Magnetic susceptibility measurements for 1 and 3 showed that one radical revealed a weak ferromagnetic interaction and an analysis by the Curie-Weiss law gave 0.3 K as theta. The other radicals examined showed weak antiferromagnetic interactions and theta 's were determined to be -0.3 to -1.5 K.
- リンク情報
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- DOI
- https://doi.org/10.1021/jo0106288
- CiNii Articles
- http://ci.nii.ac.jp/naid/80012875424
- PubMed
- https://www.ncbi.nlm.nih.gov/pubmed/11681961
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000171973700030&DestApp=WOS_CPL
- ID情報
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- DOI : 10.1021/jo0106288
- ISSN : 0022-3263
- CiNii Articles ID : 80012875424
- PubMed ID : 11681961
- Web of Science ID : WOS:000171973700030