The role of thiophenol in the proposed mechanism for one pot transformation of 2-phenylthio-3-aminocyclohexanols to dehydropiperidine derivatives
This paper describes the effect of thiophenol concentration on photochemical rearrangement of 2-phenylthio-3-aminocyclohexanols to the corresponding protected aminoaldehydes. The obtained aminoaldehyde is in equilibrium with its corresponding deoxyazasugar. The latter could be converted to the corre...
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2016-11-01
|
| Series: | Arabian Journal of Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535211002759 |
| id |
doaj-162cf4a531534f3586ee57024ac09123 |
|---|---|
| record_format |
Article |
| spelling |
doaj-162cf4a531534f3586ee57024ac091232020-11-24T20:41:22ZengElsevierArabian Journal of Chemistry1878-53522016-11-019S2S1005S100910.1016/j.arabjc.2011.10.014The role of thiophenol in the proposed mechanism for one pot transformation of 2-phenylthio-3-aminocyclohexanols to dehydropiperidine derivativesFirouzeh NematiAli AmoozadehThis paper describes the effect of thiophenol concentration on photochemical rearrangement of 2-phenylthio-3-aminocyclohexanols to the corresponding protected aminoaldehydes. The obtained aminoaldehyde is in equilibrium with its corresponding deoxyazasugar. The latter could be converted to the corresponding dehydropiperidine with a good yield in the same reaction media by controlling the thiophenol concentration. Also a proposed mechanism for this one pot transformation is reported.http://www.sciencedirect.com/science/article/pii/S1878535211002759Photo-induced electron transfer reaction2-PhenylthioalcoholDeoxyazasugarsThiophenolScavengerAb initio calculation |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Firouzeh Nemati Ali Amoozadeh |
| spellingShingle |
Firouzeh Nemati Ali Amoozadeh The role of thiophenol in the proposed mechanism for one pot transformation of 2-phenylthio-3-aminocyclohexanols to dehydropiperidine derivatives Arabian Journal of Chemistry Photo-induced electron transfer reaction 2-Phenylthioalcohol Deoxyazasugars Thiophenol Scavenger Ab initio calculation |
| author_facet |
Firouzeh Nemati Ali Amoozadeh |
| author_sort |
Firouzeh Nemati |
| title |
The role of thiophenol in the proposed mechanism for one pot transformation of 2-phenylthio-3-aminocyclohexanols to dehydropiperidine derivatives |
| title_short |
The role of thiophenol in the proposed mechanism for one pot transformation of 2-phenylthio-3-aminocyclohexanols to dehydropiperidine derivatives |
| title_full |
The role of thiophenol in the proposed mechanism for one pot transformation of 2-phenylthio-3-aminocyclohexanols to dehydropiperidine derivatives |
| title_fullStr |
The role of thiophenol in the proposed mechanism for one pot transformation of 2-phenylthio-3-aminocyclohexanols to dehydropiperidine derivatives |
| title_full_unstemmed |
The role of thiophenol in the proposed mechanism for one pot transformation of 2-phenylthio-3-aminocyclohexanols to dehydropiperidine derivatives |
| title_sort |
role of thiophenol in the proposed mechanism for one pot transformation of 2-phenylthio-3-aminocyclohexanols to dehydropiperidine derivatives |
| publisher |
Elsevier |
| series |
Arabian Journal of Chemistry |
| issn |
1878-5352 |
| publishDate |
2016-11-01 |
| description |
This paper describes the effect of thiophenol concentration on photochemical rearrangement of 2-phenylthio-3-aminocyclohexanols to the corresponding protected aminoaldehydes. The obtained aminoaldehyde is in equilibrium with its corresponding deoxyazasugar. The latter could be converted to the corresponding dehydropiperidine with a good yield in the same reaction media by controlling the thiophenol concentration. Also a proposed mechanism for this one pot transformation is reported. |
| topic |
Photo-induced electron transfer reaction 2-Phenylthioalcohol Deoxyazasugars Thiophenol Scavenger Ab initio calculation |
| url |
http://www.sciencedirect.com/science/article/pii/S1878535211002759 |
| work_keys_str_mv |
AT firouzehnemati theroleofthiophenolintheproposedmechanismforonepottransformationof2phenylthio3aminocyclohexanolstodehydropiperidinederivatives AT aliamoozadeh theroleofthiophenolintheproposedmechanismforonepottransformationof2phenylthio3aminocyclohexanolstodehydropiperidinederivatives AT firouzehnemati roleofthiophenolintheproposedmechanismforonepottransformationof2phenylthio3aminocyclohexanolstodehydropiperidinederivatives AT aliamoozadeh roleofthiophenolintheproposedmechanismforonepottransformationof2phenylthio3aminocyclohexanolstodehydropiperidinederivatives |
| _version_ |
1716825389308837888 |