A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid

A new method was developed for the direct synthesis of the second representative of the homologous series of diamond-like hydrocarbons, diamantane, in 65% yield by hydroisomerization of the norbornadiene dimer, endo-endo-heptacyclo[8.4.0.0(2,12).0(3,8).0(4,6).0(5,9).0(11,13)]tetradecane (binor-S) on...

Descripción completa

Detalles Bibliográficos
Autores principales: Aminov, Rishat I, Khusnutdinov, Ravil I
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7588729/
https://www.ncbi.nlm.nih.gov/pubmed/33133285
http://dx.doi.org/10.3762/bjoc.16.205
_version_ 1783600425737388032
author Aminov, Rishat I
Khusnutdinov, Ravil I
author_facet Aminov, Rishat I
Khusnutdinov, Ravil I
author_sort Aminov, Rishat I
collection PubMed
description A new method was developed for the direct synthesis of the second representative of the homologous series of diamond-like hydrocarbons, diamantane, in 65% yield by hydroisomerization of the norbornadiene dimer, endo-endo-heptacyclo[8.4.0.0(2,12).0(3,8).0(4,6).0(5,9).0(11,13)]tetradecane (binor-S) on treatment with concentrated sulfuric acid (98%). In the presence of H(2)SO(4) of lower concentration (75–80%), the reaction stops after the hydrogenation step giving endo-endo-pentacyclo[7.3.1.1(2,5).1(8,10).0(3,7)]tetradecane in 68% yield with excellent selectivity (100%).
format Online
Article
Text
id pubmed-7588729
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-75887292020-10-30 A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid Aminov, Rishat I Khusnutdinov, Ravil I Beilstein J Org Chem Full Research Paper A new method was developed for the direct synthesis of the second representative of the homologous series of diamond-like hydrocarbons, diamantane, in 65% yield by hydroisomerization of the norbornadiene dimer, endo-endo-heptacyclo[8.4.0.0(2,12).0(3,8).0(4,6).0(5,9).0(11,13)]tetradecane (binor-S) on treatment with concentrated sulfuric acid (98%). In the presence of H(2)SO(4) of lower concentration (75–80%), the reaction stops after the hydrogenation step giving endo-endo-pentacyclo[7.3.1.1(2,5).1(8,10).0(3,7)]tetradecane in 68% yield with excellent selectivity (100%). Beilstein-Institut 2020-10-12 /pmc/articles/PMC7588729/ /pubmed/33133285 http://dx.doi.org/10.3762/bjoc.16.205 Text en Copyright © 2020, Aminov and Khusnutdinov https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Aminov, Rishat I
Khusnutdinov, Ravil I
A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid
title A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid
title_full A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid
title_fullStr A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid
title_full_unstemmed A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid
title_short A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid
title_sort new method for the synthesis of diamantane by hydroisomerization of binor-s on treatment with sulfuric acid
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7588729/
https://www.ncbi.nlm.nih.gov/pubmed/33133285
http://dx.doi.org/10.3762/bjoc.16.205
work_keys_str_mv AT aminovrishati anewmethodforthesynthesisofdiamantanebyhydroisomerizationofbinorsontreatmentwithsulfuricacid
AT khusnutdinovravili anewmethodforthesynthesisofdiamantanebyhydroisomerizationofbinorsontreatmentwithsulfuricacid
AT aminovrishati newmethodforthesynthesisofdiamantanebyhydroisomerizationofbinorsontreatmentwithsulfuricacid
AT khusnutdinovravili newmethodforthesynthesisofdiamantanebyhydroisomerizationofbinorsontreatmentwithsulfuricacid

Ejemplares similares