Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1 S,5 R,8 R) and (1 R,5 S,8 S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate
Treament of (+)limonene with diluted perchloric acid in acetonitrile solution afforded (1 S,5 R,8 R) 8-acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate while the same reaction on (—)β-pinene produced the (1 R,5 S,8 S) enantiomer, and terpinolene gave the racemic mixture. The s...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_09320776_v39_n7_p972_Caram |
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todo:paper_09320776_v39_n7_p972_Caram2023-10-03T15:48:23Z Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1 S,5 R,8 R) and (1 R,5 S,8 S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate Caram, J. Martins, M.E. Marschoff, C.M. Cafferata, L.F.R. Gros, E.G. (+)Limonene (—)β-Pinene Ritter Reaction Stereospecific Synthesis Terpinolene Treament of (+)limonene with diluted perchloric acid in acetonitrile solution afforded (1 S,5 R,8 R) 8-acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate while the same reaction on (—)β-pinene produced the (1 R,5 S,8 S) enantiomer, and terpinolene gave the racemic mixture. The structure of 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. © 1984, IEEE. All rights reserved. Fil:Caram, J. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Marschoff, C.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Gros, E.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_09320776_v39_n7_p972_Caram |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
(+)Limonene (—)β-Pinene Ritter Reaction Stereospecific Synthesis Terpinolene |
| spellingShingle |
(+)Limonene (—)β-Pinene Ritter Reaction Stereospecific Synthesis Terpinolene Caram, J. Martins, M.E. Marschoff, C.M. Cafferata, L.F.R. Gros, E.G. Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1 S,5 R,8 R) and (1 R,5 S,8 S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate |
| topic_facet |
(+)Limonene (—)β-Pinene Ritter Reaction Stereospecific Synthesis Terpinolene |
| description |
Treament of (+)limonene with diluted perchloric acid in acetonitrile solution afforded (1 S,5 R,8 R) 8-acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate while the same reaction on (—)β-pinene produced the (1 R,5 S,8 S) enantiomer, and terpinolene gave the racemic mixture. The structure of 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. © 1984, IEEE. All rights reserved. |
| format |
JOUR |
| author |
Caram, J. Martins, M.E. Marschoff, C.M. Cafferata, L.F.R. Gros, E.G. |
| author_facet |
Caram, J. Martins, M.E. Marschoff, C.M. Cafferata, L.F.R. Gros, E.G. |
| author_sort |
Caram, J. |
| title |
Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1 S,5 R,8 R) and (1 R,5 S,8 S) 8-Acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene Perchlorate |
| title_short |
Ritter Reaction on Terpenoids, I Stereospecific Preparation of (1 S,5 R,8 R) and (1 R,5 S,8 S) 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 (1 S,5 R,8 R) and (1 R,5 S,8 S) 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 (1 S,5 R,8 R) and (1 R,5 S,8 S) 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 (1 S,5 R,8 R) and (1 R,5 S,8 S) 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 (1 s,5 r,8 r) and (1 r,5 s,8 s) 8-acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1]non-2-ene perchlorate |
| url |
http://hdl.handle.net/20.500.12110/paper_09320776_v39_n7_p972_Caram |
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