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Issue 16, 2019
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Donor–acceptor-stabilised germanium analogues of acid chloride, ester, and acyl pyrrole compounds: synthesis and reactivity

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Abstract

Germaacid chloride, germaester, and N-germaacyl pyrrole compounds were not known previously. Therefore, donor–acceptor-stabilised germaacid chloride (i-Bu)2ATIGe(O)(Cl) → B(C6F5)3 (1), germaester (i-Bu)2ATIGe(O)(OSiPh3) → B(C6F5)3 (2), and N-germaacyl pyrrole (i-Bu)2ATIGe(O)(NC4H4) → B(C6F5)3 (3) compounds, with Cl–Ge[double bond, length as m-dash]O, Ph3SiO–Ge[double bond, length as m-dash]O, and C4H4N–Ge[double bond, length as m-dash]O moieties, respectively, are reported here. Germaacid chloride 1 reacts with PhCCLi, KOt-Bu, and RLi (R = Ph, Me) to afford donor–acceptor-stabilised germaynone (i-Bu)2ATIGe(O)(CCPh) → B(C6F5)3 (4), germaester (i-Bu)2ATIGe(O)(Ot-Bu) → B(C6F5)3 (5), and germanone (i-Bu)2ATIGe(O)(R) → B(C6F5)3 (R = Ph 6, Me 7) compounds, respectively. Interconversion between a germaester and a germaacid chloride is achieved; reaction of germaesters 2 and 5 with TMSCl gave germaacid chloride 1, and 1 reacted with Ph3SiOLi and KOt-Bu to produce germaesters 2 and 5. Reaction of N-germaacyl pyrrole 3 with thiophenol produced a donor–acceptor-stabilised germaacyl thioester (i-Bu)2ATIGe(O)(SPh) → B(C6F5)3 (10). Furthermore, the attempted syntheses of germaamides and germacarboxylic acids are also discussed.

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

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Publication details

The article was received on 02 Dec 2018, accepted on 17 Feb 2019 and first published on 18 Feb 2019


Article type: Edge Article
DOI: 10.1039/C8SC05380D
Citation: Chem. Sci., 2019,10, 4402-4411
  • Open access: Creative Commons BY-NC license
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    Donor–acceptor-stabilised germanium analogues of acid chloride, ester, and acyl pyrrole compounds: synthesis and reactivity

    M. K. Sharma, S. Sinhababu, P. Mahawar, G. Mukherjee, B. Pandey, G. Rajaraman and S. Nagendran, Chem. Sci., 2019, 10, 4402
    DOI: 10.1039/C8SC05380D

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