| Item type |
デフォルトアイテムタイプ_（フル）(1) |
| 公開日 |
2023-03-18 |
| タイトル |
|
|
タイトル |
Synthesis and application of a bidentate ligand based on decafluoro-3-phenyl-3-pentanol : Steric effect of pentafluoroethyl groups on the stereomutation of O-equatorial C-apical spirophosphoranes |
|
言語 |
en |
| 作成者 |
Jiang, Xin-Dong
Kakuda, Ken-ichiro
Matsukawa, Shiro
Yamamichi, Hideaki
Kojima, Satoshi
Yamamoto, Yohsuke
|
| アクセス権 |
|
|
アクセス権 |
open access |
|
アクセス権URI |
http://purl.org/coar/access_right/c_abf2 |
| 権利情報 |
|
|
権利情報 |
Copyright (c) 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
| 主題 |
|
|
主題Scheme |
Other |
|
主題 |
hypervalent compounds |
| 主題 |
|
|
主題Scheme |
Other |
|
主題 |
isomerization |
| 主題 |
|
|
主題Scheme |
Other |
|
主題 |
spiro compounds |
| 主題 |
|
|
主題Scheme |
Other |
|
主題 |
steric hindrance |
| 主題 |
|
|
主題Scheme |
Other |
|
主題 |
X-ray diffraction |
| 主題 |
|
|
主題Scheme |
NDC |
|
主題 |
430 |
| 内容記述 |
|
|
内容記述 |
1,1,1,2,2,4,4,5,5,5-Decafluoro-3-phenyl-3-pentanol (13) was prepared via the Cannizzaro-type disproportionation reaction, and dimetallated 13 (i.e., 15) was used as a bidentate ligand, which was bulkier than the Martin ligand (1,1,1,3,3,3-hexafluoro-2-phenyl-2-propanol). P-H spirophosphorane (16) was synthesized utilizing the new bidentate ligand, and the structure of 16 was essentially the same as that of the P-H phosphorane with the Martin ligands (1b). Phosphoranes which exhibit reversed apicophilicity (9: O-equatorial) were also synthesized and could be converted to the corresponding stable stereoisomers (10: O-apical). The crystal structures of O-equatorial phosphoranes (9) and those of O-apical isomers (10) were slightly affected by the steric repulsion of pentafluoroethyl groups. Kinetic measurements revealed that the stereomutation of O-equatorial methylphosphorane (9a) to the O-apical isomer (10a) was slowed. The activation enthalpy for the stereomutation of 9a→10a (24.4 kcal mol–1) was higher than that of the phosphorane bearing the Martin ligands (3a→4a: 19.3 kcal mol–1) by 5.1 kcal mol–1. |
|
言語 |
en |
| 出版者 |
|
|
出版者 |
Wiley-VCH Verlag GmbH |
| 言語 |
|
|
言語 |
eng |
| 資源タイプ |
|
|
資源タイプ識別子 |
http://purl.org/coar/resource_type/c_6501 |
|
資源タイプ |
journal article |
| 出版タイプ |
|
|
出版タイプ |
AO |
|
出版タイプResource |
http://purl.org/coar/version/c_b1a7d7d4d402bcce |
| 関連情報 |
|
|
|
識別子タイプ |
DOI |
|
|
関連識別子 |
10.1002/asia.200600334 |
| 関連情報 |
|
|
|
識別子タイプ |
DOI |
|
|
関連識別子 |
http://dx.doi.org/10.1002/asia.200600334 |
| 収録物識別子 |
|
|
収録物識別子タイプ |
ISSN |
|
収録物識別子 |
1861-4728 |
| 収録物識別子 |
|
|
収録物識別子タイプ |
NCID |
|
収録物識別子 |
AA12151701 |
| 開始ページ |
|
|
開始ページ |
314 |
| 書誌情報 |
Chemistry - An Asian Journal
Chemistry - An Asian Journal
巻 2,
号 2,
p. 314-323,
発行日 2007
|
| 旧ID |
20645 |
ChemAsianJ_2-2_314.pdf (1.2 MB)
