Treatment of Alcohols with Tosyl Chloride Does Not always Lead to the Formation of Tosylates
Treatment of substituted benzyl alcohols with tosyl chloride resulted in the formation of the corresponding chlorides, not the usual tosylates. A series of experiments demonstrated that it was possible to predict whether chlorination or tosylation would occur for substituted benzyl alcohols and pyri...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2011-07-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/16/7/5665/ |
| _version_ | 1817979466822975488 |
|---|---|
| author | Chuanmin Qi Yurong Chen Man Feng Xiao Wang Rui Ding Jingli Xu Yong He |
| author_facet | Chuanmin Qi Yurong Chen Man Feng Xiao Wang Rui Ding Jingli Xu Yong He |
| author_sort | Chuanmin Qi |
| collection | DOAJ |
| description | Treatment of substituted benzyl alcohols with tosyl chloride resulted in the formation of the corresponding chlorides, not the usual tosylates. A series of experiments demonstrated that it was possible to predict whether chlorination or tosylation would occur for substituted benzyl alcohols and pyridine methanols. Treatment of electron withdrawing group-substituted benzyl alcohols with tosyl chloride gave the corresponding chlorides in moderate yields under mild conditions, which provided a simple way to directly prepare chlorides from alcohols. |
| first_indexed | 2024-04-13T22:42:17Z |
| format | Article |
| id | doaj.art-da92329e3bfc4eb088c3e9b5dd2c615d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T22:42:17Z |
| publishDate | 2011-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-da92329e3bfc4eb088c3e9b5dd2c615d2022-12-22T02:26:34ZengMDPI AGMolecules1420-30492011-07-011675665567310.3390/molecules16075665Treatment of Alcohols with Tosyl Chloride Does Not always Lead to the Formation of TosylatesChuanmin QiYurong ChenMan FengXiao WangRui DingJingli XuYong HeTreatment of substituted benzyl alcohols with tosyl chloride resulted in the formation of the corresponding chlorides, not the usual tosylates. A series of experiments demonstrated that it was possible to predict whether chlorination or tosylation would occur for substituted benzyl alcohols and pyridine methanols. Treatment of electron withdrawing group-substituted benzyl alcohols with tosyl chloride gave the corresponding chlorides in moderate yields under mild conditions, which provided a simple way to directly prepare chlorides from alcohols.http://www.mdpi.com/1420-3049/16/7/5665/tosyl chloridechlorinationtosylationbenzyl alcoholspyridine methanols |
| spellingShingle | Chuanmin Qi Yurong Chen Man Feng Xiao Wang Rui Ding Jingli Xu Yong He Treatment of Alcohols with Tosyl Chloride Does Not always Lead to the Formation of Tosylates Molecules tosyl chloride chlorination tosylation benzyl alcohols pyridine methanols |
| title | Treatment of Alcohols with Tosyl Chloride Does Not always Lead to the Formation of Tosylates |
| title_full | Treatment of Alcohols with Tosyl Chloride Does Not always Lead to the Formation of Tosylates |
| title_fullStr | Treatment of Alcohols with Tosyl Chloride Does Not always Lead to the Formation of Tosylates |
| title_full_unstemmed | Treatment of Alcohols with Tosyl Chloride Does Not always Lead to the Formation of Tosylates |
| title_short | Treatment of Alcohols with Tosyl Chloride Does Not always Lead to the Formation of Tosylates |
| title_sort | treatment of alcohols with tosyl chloride does not always lead to the formation of tosylates |
| topic | tosyl chloride chlorination tosylation benzyl alcohols pyridine methanols |
| url | http://www.mdpi.com/1420-3049/16/7/5665/ |
| work_keys_str_mv | AT chuanminqi treatmentofalcoholswithtosylchloridedoesnotalwaysleadtotheformationoftosylates AT yurongchen treatmentofalcoholswithtosylchloridedoesnotalwaysleadtotheformationoftosylates AT manfeng treatmentofalcoholswithtosylchloridedoesnotalwaysleadtotheformationoftosylates AT xiaowang treatmentofalcoholswithtosylchloridedoesnotalwaysleadtotheformationoftosylates AT ruiding treatmentofalcoholswithtosylchloridedoesnotalwaysleadtotheformationoftosylates AT jinglixu treatmentofalcoholswithtosylchloridedoesnotalwaysleadtotheformationoftosylates AT yonghe treatmentofalcoholswithtosylchloridedoesnotalwaysleadtotheformationoftosylates |