Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1S,5R,8R) and (1R,5S,8S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate

Treament of ( + )lim onene with diluted perchloric acid in acetonitrile solution afforded (1S, 5R, 8R) 8-acetam ido-2,4,4.8-tetram ethyl-3-aza-bicyclo[3.3.1]non-2-ene perchlorate while the same reaction on ( — )β-pinene produced the (1S, 5R, 8R) enantiom er, and terpinolene gave the racemic mixture....

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Detalhes bibliográficos
Autores: Caram, José Alberto, Martins, María Elisa, Marschoff, Carlos Miguel, Cafferata, Lázaro F. R.
Tipo de documento: artigo
Estado:Versão publicada
Data de publicação:1984
País:Argentina
Recursos:Universidad Nacional de La Plata
Repositório:SEDICI (UNLP)
Idioma:inglês
OAI Identifier:oai:sedici.unlp.edu.ar:10915/120779
Acesso em linha:http://sedici.unlp.edu.ar/handle/10915/120779
Access Level:Acceso aberto
Palavra-chave:Química
Ritter Reaction
(+)Limonene
( -)β-Pinene
Terpinolene
Stereospecific synthesis
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spelling Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1S,5R,8R) and (1R,5S,8S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene PerchlorateCaram, José AlbertoMartins, María ElisaMarschoff, Carlos MiguelCafferata, Lázaro F. R.QuímicaRitter Reaction(+)Limonene( -)β-PineneTerpinoleneStereospecific synthesisTreament of ( + )lim onene with diluted perchloric acid in acetonitrile solution afforded (1S, 5R, 8R) 8-acetam ido-2,4,4.8-tetram ethyl-3-aza-bicyclo[3.3.1]non-2-ene perchlorate while the same reaction on ( — )β-pinene produced the (1S, 5R, 8R) enantiom er, and terpinolene gave the racemic mixture. The structure o f the product is proposed on basis of its physical and spectroscopic (IR , ¹H and ¹³C NMR, MS) properties and its formation involves a Ritter reaction between the monoterpene and acetonitrile.Publicado on line en 2014.Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas1984info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf972-974http://sedici.unlp.edu.ar/handle/10915/120779enginfo:eu-repo/semantics/altIdentifier/issn/1865-7117info:eu-repo/semantics/altIdentifier/doi/10.1515/znb-1984-0722info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-nd/3.0/Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported (CC BY-NC-ND 3.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2024-05-08T13:06:44Zoai:sedici.unlp.edu.ar:10915/120779Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292024-05-08 13:06:45.191SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1S,5R,8R) and (1R,5S,8S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate
title Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1S,5R,8R) and (1R,5S,8S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate
spellingShingle Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1S,5R,8R) and (1R,5S,8S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate
Caram, José Alberto
Química
Ritter Reaction
(+)Limonene
( -)β-Pinene
Terpinolene
Stereospecific synthesis
title_short Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1S,5R,8R) and (1R,5S,8S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate
title_full Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1S,5R,8R) and (1R,5S,8S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate
title_fullStr Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1S,5R,8R) and (1R,5S,8S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate
title_full_unstemmed Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1S,5R,8R) and (1R,5S,8S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate
title_sort Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1S,5R,8R) and (1R,5S,8S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate
dc.creator.none.fl_str_mv Caram, José Alberto
Martins, María Elisa
Marschoff, Carlos Miguel
Cafferata, Lázaro F. R.
author Caram, José Alberto
author_facet Caram, José Alberto
Martins, María Elisa
Marschoff, Carlos Miguel
Cafferata, Lázaro F. R.
author_role author
author2 Martins, María Elisa
Marschoff, Carlos Miguel
Cafferata, Lázaro F. R.
author2_role author
author
author
dc.subject.none.fl_str_mv Química
Ritter Reaction
(+)Limonene
( -)β-Pinene
Terpinolene
Stereospecific synthesis
topic Química
Ritter Reaction
(+)Limonene
( -)β-Pinene
Terpinolene
Stereospecific synthesis
description Treament of ( + )lim onene with diluted perchloric acid in acetonitrile solution afforded (1S, 5R, 8R) 8-acetam ido-2,4,4.8-tetram ethyl-3-aza-bicyclo[3.3.1]non-2-ene perchlorate while the same reaction on ( — )β-pinene produced the (1S, 5R, 8R) enantiom er, and terpinolene gave the racemic mixture. The structure o f the product is proposed on basis of its physical and spectroscopic (IR , ¹H and ¹³C NMR, MS) properties and its formation involves a Ritter reaction between the monoterpene and acetonitrile.
publishDate 1984
dc.date.none.fl_str_mv 1984
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://sedici.unlp.edu.ar/handle/10915/120779
url http://sedici.unlp.edu.ar/handle/10915/120779
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/1865-7117
info:eu-repo/semantics/altIdentifier/doi/10.1515/znb-1984-0722
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/3.0/
Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported (CC BY-NC-ND 3.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-nd/3.0/
Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported (CC BY-NC-ND 3.0)
dc.format.none.fl_str_mv application/pdf
972-974
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
instname:Universidad Nacional de La Plata
instacron:UNLP
instname_str Universidad Nacional de La Plata
instacron_str UNLP
institution UNLP
reponame_str SEDICI (UNLP)
collection SEDICI (UNLP)
repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
repository.mail.fl_str_mv alira@sedici.unlp.edu.ar
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score 15.812429

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