{"title":"Concise Synthesis of Monocarbamate-Cyclohexanetriacetate from Allylic Bis-Carbamate","authors":"L. Kelebekli","doi":"10.1134/S1070363225602261","DOIUrl":null,"url":null,"abstract":"<p>The concise synthesis of novel monocarbamate-triacetate with a configuration like that of <i>cis-trans-cis</i>-cyclohexanetetrol is reported for the first time. Photooxygenation reaction of the starting compound cyclohexadiene gave the bicyclic endoperoxide compound. Controlled reduction of the endoperoxide with thiourea afforded the allylic <i>cis</i>-diol compound, and subsequent reaction of the <i>cis</i>-diol with two equivalents of <i>p</i>-TsNCO led to the formation of the key compound bis-carbamate. Treatment of the bis-carbamate compound with Pd<sub>2</sub>(dba)<sub>3</sub>·CHCl<sub>3</sub> in the presence of trimethylsilyl azide (TMSN<sub>3</sub>) produced a new monocarbamate compound as well as an oxazolidinone derivative. By oxidation of the double bond in the monocarbamate with osmium tetraoxide and subsequent acetylation with AcCl, a desired new monocarbamate triacetate compound was obtained.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"95 9","pages":"2528 - 2536"},"PeriodicalIF":0.8000,"publicationDate":"2025-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Journal of General Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1134/S1070363225602261","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
The concise synthesis of novel monocarbamate-triacetate with a configuration like that of cis-trans-cis-cyclohexanetetrol is reported for the first time. Photooxygenation reaction of the starting compound cyclohexadiene gave the bicyclic endoperoxide compound. Controlled reduction of the endoperoxide with thiourea afforded the allylic cis-diol compound, and subsequent reaction of the cis-diol with two equivalents of p-TsNCO led to the formation of the key compound bis-carbamate. Treatment of the bis-carbamate compound with Pd2(dba)3·CHCl3 in the presence of trimethylsilyl azide (TMSN3) produced a new monocarbamate compound as well as an oxazolidinone derivative. By oxidation of the double bond in the monocarbamate with osmium tetraoxide and subsequent acetylation with AcCl, a desired new monocarbamate triacetate compound was obtained.
期刊介绍：
Russian Journal of General Chemistry is a journal that covers many problems that are of general interest to the whole community of chemists. The journal is the successor to Russia’s first chemical journal, Zhurnal Russkogo Khimicheskogo Obshchestva (Journal of the Russian Chemical Society ) founded in 1869 to cover all aspects of chemistry. Now the journal is focused on the interdisciplinary areas of chemistry (organometallics, organometalloids, organoinorganic complexes, mechanochemistry, nanochemistry, etc.), new achievements and long-term results in the field. The journal publishes reviews, current scientific papers, letters to the editor, and discussion papers.
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