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供体-受体稳定的酰氯、酯和酰基吡咯化合物的锗类似物：合成与反应活性

Donor-acceptor-stabilised germanium analogues of acid chloride, ester, and acyl pyrrole compounds: synthesis and reactivity.

作者信息

Sharma Mahendra Kumar, Sinhababu Soumen, Mahawar Pritam, Mukherjee Goutam, Pandey Bhawana, Rajaraman Gopalan, Nagendran Selvarajan

机构信息

Department of Chemistry , Indian Institute of Technology Delhi , Hauz Khas , New Delhi 110 016 , India . Email:

Department of Chemistry , Indian Institute of Technology Bombay , Powai , Mumbai 400076 , India.

出版信息

Chem Sci. 2019 Feb 18;10(16):4402-4411. doi: 10.1039/c8sc05380d. eCollection 2019 Apr 28.

DOI:10.1039/c8sc05380d
PMID:31057767
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6472437/
Abstract

Germaacid chloride, germaester, and -germaacyl pyrrole compounds were not known previously. Therefore, donor-acceptor-stabilised germaacid chloride (i-Bu)ATIGe(O)(Cl) → B(CF) (), germaester (i-Bu)ATIGe(O)(OSiPh) → B(CF) (), and -germaacyl pyrrole (i-Bu)ATIGe(O)(NCH) → B(CF) () compounds, with Cl-Ge[double bond, length as m-dash]O, PhSiO-Ge[double bond, length as m-dash]O, and CHN-Ge[double bond, length as m-dash]O moieties, respectively, are reported here. Germaacid chloride reacts with PhCCLi, KO-Bu, and RLi (R = Ph, Me) to afford donor-acceptor-stabilised germaynone (i-Bu)ATIGe(O)(CCPh) → B(CF) (), germaester (i-Bu)ATIGe(O)(O-Bu) → B(CF) (), and germanone (i-Bu)ATIGe(O)(R) → B(CF) (R = Ph , Me ) compounds, respectively. Interconversion between a germaester and a germaacid chloride is achieved; reaction of germaesters and with TMSCl gave germaacid chloride , and reacted with PhSiOLi and KO-Bu to produce germaesters and . Reaction of -germaacyl pyrrole with thiophenol produced a donor-acceptor-stabilised germaacyl thioester (i-Bu)ATIGe(O)(SPh) → B(CF) (). Furthermore, the attempted syntheses of germaamides and germacarboxylic acids are also discussed.

摘要

锗酰氯、锗酯和 - 锗酰基吡咯化合物以前并不为人所知。因此，本文报道了供体 - 受体稳定的锗酰氯（i - Bu）ATIGe（O）（Cl）→B（CF）（）、锗酯（i - Bu）ATIGe（O）（OSiPh）→B（CF）（）和 - 锗酰基吡咯（i - Bu）ATIGe（O）（NCH）→B（CF）（）化合物，它们分别具有 Cl - Ge═O、PhSiO - Ge═O 和 CHN - Ge═O 部分。锗酰氯 与 PhCCLi、KO - Bu 和 RLi（R = Ph，Me）反应，分别得到供体 - 受体稳定的锗酮（i - Bu）ATIGe（O）（CCPh）→B（CF）（）、锗酯（i - Bu）ATIGe（O）（O - Bu）→B（CF）（）和锗酮（i - Bu）ATIGe（O）（R）→B（CF）（R = Ph ，Me ）化合物。实现了锗酯和锗酰氯之间的相互转化；锗酯 和 与 TMSCl 反应生成锗酰氯 ， 与 PhSiOLi 和 KO - Bu 反应生成锗酯 和 。- 锗酰基吡咯 与苯硫酚反应生成供体 - 受体稳定的锗酰硫酯（i - Bu）ATIGe（O）（SPh）→B（CF）（）。此外，还讨论了锗酰胺和锗羧酸的合成尝试。

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