Unique Stereocontrol in Carborane Chemistry: Skeletal Alkylcarbonation (SAC) versus Exoskeletal Alkylmethylation (EAM) Reactions
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F15%3A39900093" target="_blank" >RIV/00216275:25310/15:39900093 - isvavai.cz</a>
Alternative codes found
RIV/61388980:_____/15:00443607
Result on the web
<a href="http://dx.doi.org/10.1002/anie.201500824" target="_blank" >http://dx.doi.org/10.1002/anie.201500824</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/anie.201500824" target="_blank" >10.1002/anie.201500824</a>
Alternative languages
Result language
angličtina
Original language name
Unique Stereocontrol in Carborane Chemistry: Skeletal Alkylcarbonation (SAC) versus Exoskeletal Alkylmethylation (EAM) Reactions
Original language description
Reactions between the arachno-6,9-C2B8H14 (1) dicarbaborane and acyl chlorides, RCOCl (2), are subject to stereocontrol that completely changes the nature of the reaction products. While most chlorides produce the 8-R-nido-7,8,9-C3B8H11 (3) tricarbollides (by skeletal alkylcarbonation=SAC), bulky RCOCls (2; where R=1-adamantyl, 2a; 1-mesityl, 2b; 9-anthranyl, 2c; 1-naphthyl, 2d) in 1,2-dichloroethane (DCE) in the presence of triethylamine at 40-60 degrees C gave a series of entirely different 1-R-2-CH3-closo-1,6-C2B8H8 (4) dicarbaboranes upon acidification with conc. H2SO4 (by exosleletal alkylmehylation=EAM). Both types of reactions seem to proceed via a common [8-R-nido-7,8,9-C3B8H10](-) (3(-)) anion which in the EAM case is unstable because of steric crowd and undergoes rearrangement via the isomeric [R-nido-7,8,10-C3B8H10](-) tricarbollide structures which, on protonation, undergo reductive extraction of one CH vertex to generate the 2-CH3 substituent in structure 4.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CA - Inorganic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/GAP207%2F11%2F0705" target="_blank" >GAP207/11/0705: Carborane-modified iron-arene complexes</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Angewandte Chemie (International Edition)
ISSN
1433-7851
e-ISSN
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Volume of the periodical
54
Issue of the periodical within the volume
16
Country of publishing house
DE - GERMANY
Number of pages
4
Pages from-to
4937-4940
UT code for WoS article
000352622400047
EID of the result in the Scopus database
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