An anomalous addition of chlorosulfonyl isocyanate to a carbonyl group: the synthesis of ((3aS,7aR,E)-2-ethyl-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-ylidene)sulfamoyl chloride
In this study, we developed a new addition reaction of chlorosulfonyl isocyanate (CSI), starting from 2-ethyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione. The addition reaction of CSI with 2-ethyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione resulted in the formation of ylidenesulfamoyl chlor...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2019-04-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.15.89 |
| id |
doaj-3f28960b22fe44e3be41bb76df3fdd91 |
|---|---|
| record_format |
Article |
| spelling |
doaj-3f28960b22fe44e3be41bb76df3fdd912021-02-02T05:36:34ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972019-04-0115193193610.3762/bjoc.15.891860-5397-15-89An anomalous addition of chlorosulfonyl isocyanate to a carbonyl group: the synthesis of ((3aS,7aR,E)-2-ethyl-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-ylidene)sulfamoyl chlorideAytekin Köse0Aslı Ünal1Ertan Şahin2Uğur Bozkaya3Yunus Kara4Department of Chemistry, Aksaray University, 68100 Aksaray, TurkeyDepartment of Chemistry, Hacettepe University, 06800 Ankara, TurkeyDepartment of Chemistry, Atatürk University, 25240 Erzurum, TurkeyDepartment of Chemistry, Hacettepe University, 06800 Ankara, TurkeyDepartment of Chemistry, Atatürk University, 25240 Erzurum, TurkeyIn this study, we developed a new addition reaction of chlorosulfonyl isocyanate (CSI), starting from 2-ethyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione. The addition reaction of CSI with 2-ethyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione resulted in the formation of ylidenesulfamoyl chloride, whose exact configuration was determined by X-ray crystal analysis. We explain the mechanism of product formation supported by theoretical calculations.https://doi.org/10.3762/bjoc.15.89addition reactionchlorosulfonyl isocyanatesulfamoyl chloridetheoretical calculations |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Aytekin Köse Aslı Ünal Ertan Şahin Uğur Bozkaya Yunus Kara |
| spellingShingle |
Aytekin Köse Aslı Ünal Ertan Şahin Uğur Bozkaya Yunus Kara An anomalous addition of chlorosulfonyl isocyanate to a carbonyl group: the synthesis of ((3aS,7aR,E)-2-ethyl-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-ylidene)sulfamoyl chloride Beilstein Journal of Organic Chemistry addition reaction chlorosulfonyl isocyanate sulfamoyl chloride theoretical calculations |
| author_facet |
Aytekin Köse Aslı Ünal Ertan Şahin Uğur Bozkaya Yunus Kara |
| author_sort |
Aytekin Köse |
| title |
An anomalous addition of chlorosulfonyl isocyanate to a carbonyl group: the synthesis of ((3aS,7aR,E)-2-ethyl-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-ylidene)sulfamoyl chloride |
| title_short |
An anomalous addition of chlorosulfonyl isocyanate to a carbonyl group: the synthesis of ((3aS,7aR,E)-2-ethyl-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-ylidene)sulfamoyl chloride |
| title_full |
An anomalous addition of chlorosulfonyl isocyanate to a carbonyl group: the synthesis of ((3aS,7aR,E)-2-ethyl-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-ylidene)sulfamoyl chloride |
| title_fullStr |
An anomalous addition of chlorosulfonyl isocyanate to a carbonyl group: the synthesis of ((3aS,7aR,E)-2-ethyl-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-ylidene)sulfamoyl chloride |
| title_full_unstemmed |
An anomalous addition of chlorosulfonyl isocyanate to a carbonyl group: the synthesis of ((3aS,7aR,E)-2-ethyl-3-oxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-ylidene)sulfamoyl chloride |
| title_sort |
anomalous addition of chlorosulfonyl isocyanate to a carbonyl group: the synthesis of ((3as,7ar,e)-2-ethyl-3-oxo-2,3,3a,4,7,7a-hexahydro-1h-isoindol-1-ylidene)sulfamoyl chloride |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2019-04-01 |
| description |
In this study, we developed a new addition reaction of chlorosulfonyl isocyanate (CSI), starting from 2-ethyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione. The addition reaction of CSI with 2-ethyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione resulted in the formation of ylidenesulfamoyl chloride, whose exact configuration was determined by X-ray crystal analysis. We explain the mechanism of product formation supported by theoretical calculations. |
| topic |
addition reaction chlorosulfonyl isocyanate sulfamoyl chloride theoretical calculations |
| url |
https://doi.org/10.3762/bjoc.15.89 |
| work_keys_str_mv |
AT aytekinkose ananomalousadditionofchlorosulfonylisocyanatetoacarbonylgroupthesynthesisof3as7are2ethyl3oxo233a477ahexahydro1hisoindol1ylidenesulfamoylchloride AT aslıunal ananomalousadditionofchlorosulfonylisocyanatetoacarbonylgroupthesynthesisof3as7are2ethyl3oxo233a477ahexahydro1hisoindol1ylidenesulfamoylchloride AT ertansahin ananomalousadditionofchlorosulfonylisocyanatetoacarbonylgroupthesynthesisof3as7are2ethyl3oxo233a477ahexahydro1hisoindol1ylidenesulfamoylchloride AT ugurbozkaya ananomalousadditionofchlorosulfonylisocyanatetoacarbonylgroupthesynthesisof3as7are2ethyl3oxo233a477ahexahydro1hisoindol1ylidenesulfamoylchloride AT yunuskara ananomalousadditionofchlorosulfonylisocyanatetoacarbonylgroupthesynthesisof3as7are2ethyl3oxo233a477ahexahydro1hisoindol1ylidenesulfamoylchloride AT aytekinkose anomalousadditionofchlorosulfonylisocyanatetoacarbonylgroupthesynthesisof3as7are2ethyl3oxo233a477ahexahydro1hisoindol1ylidenesulfamoylchloride AT aslıunal anomalousadditionofchlorosulfonylisocyanatetoacarbonylgroupthesynthesisof3as7are2ethyl3oxo233a477ahexahydro1hisoindol1ylidenesulfamoylchloride AT ertansahin anomalousadditionofchlorosulfonylisocyanatetoacarbonylgroupthesynthesisof3as7are2ethyl3oxo233a477ahexahydro1hisoindol1ylidenesulfamoylchloride AT ugurbozkaya anomalousadditionofchlorosulfonylisocyanatetoacarbonylgroupthesynthesisof3as7are2ethyl3oxo233a477ahexahydro1hisoindol1ylidenesulfamoylchloride AT yunuskara anomalousadditionofchlorosulfonylisocyanatetoacarbonylgroupthesynthesisof3as7are2ethyl3oxo233a477ahexahydro1hisoindol1ylidenesulfamoylchloride |
| _version_ |
1724303257981943808 |