左旋葡萄糖酮和异左旋葡萄糖酮Diels-Alder加合物的合成和操作

IF 1 4区化学 Q4 CHEMISTRY, MULTIDISCIPLINARY

Australian Journal of Chemistry Pub Date : 2023-01-01 DOI:10.1071/ch23130

Brett Pollard, Xin Liu, Luke A. Connal, Martin G. Banwell, Michael G. Gardiner

{"title":"左旋葡萄糖酮和异左旋葡萄糖酮Diels-Alder加合物的合成和操作","authors":"Brett Pollard, Xin Liu, Luke A. Connal, Martin G. Banwell, Michael G. Gardiner","doi":"10.1071/ch23130","DOIUrl":null,"url":null,"abstract":"Diels–Alder cycloaddition reactions between the biomass-derived platform molecule levoglucosenone (2) and various cyclic dienes such as α-terpinene produced a range of adducts, including compound 28. Manipulation of these adducts then afforded a series of derivatives. So, for example, reductions of the associated carbonyl groups delivered the corresponding alcohols including compound 29 and on reaction of these with diethylaminosulfur trifluoride rearranged fluorination products such as tetracycle 30 were obtained. An analogous suite of compounds was obtained by manipulation of the Diels–Alder adducts derived from reacting the same dienes with iso-levoglucosenone that was itself obtained through simple manipulation of levoglucosenone. Our earlier studies suggest that various of these derivatives could be used in the production, via ring-opening metathesis polymerisation (ROMP), of new bio-based polymers.","PeriodicalId":8575,"journal":{"name":"Australian Journal of Chemistry","volume":"16 1","pages":"0"},"PeriodicalIF":1.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"The synthesis and manipulation of certain Diels–Alder adducts of levoglucosenone and iso-levoglucosenone\",\"authors\":\"Brett Pollard, Xin Liu, Luke A. Connal, Martin G. Banwell, Michael G. Gardiner\",\"doi\":\"10.1071/ch23130\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Diels–Alder cycloaddition reactions between the biomass-derived platform molecule levoglucosenone (2) and various cyclic dienes such as α-terpinene produced a range of adducts, including compound 28. Manipulation of these adducts then afforded a series of derivatives. So, for example, reductions of the associated carbonyl groups delivered the corresponding alcohols including compound 29 and on reaction of these with diethylaminosulfur trifluoride rearranged fluorination products such as tetracycle 30 were obtained. An analogous suite of compounds was obtained by manipulation of the Diels–Alder adducts derived from reacting the same dienes with iso-levoglucosenone that was itself obtained through simple manipulation of levoglucosenone. Our earlier studies suggest that various of these derivatives could be used in the production, via ring-opening metathesis polymerisation (ROMP), of new bio-based polymers.\",\"PeriodicalId\":8575,\"journal\":{\"name\":\"Australian Journal of Chemistry\",\"volume\":\"16 1\",\"pages\":\"0\"},\"PeriodicalIF\":1.0000,\"publicationDate\":\"2023-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Australian Journal of Chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1071/ch23130\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Australian Journal of Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1071/ch23130","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

摘要

生物来源的平台分子左旋葡萄糖酮(2)与各种环二烯(如α-萜烯)之间的Diels-Alder环加成反应产生了一系列加合物，包括化合物28。对这些加合物的操纵产生了一系列的衍生物。因此，例如，相关羰基的还原产生了相应的醇，包括化合物29，并与二乙基氨基三氟化硫重排氟化产物，如四环30反应得到。通过操纵Diels-Alder加合物得到类似的一组化合物，这些加合物是由相同的二烯与异左旋葡萄糖酮反应产生的，而异左旋葡萄糖酮本身是通过简单的左旋葡萄糖酮操作得到的。我们早期的研究表明，各种这些衍生物可以用于生产，通过开环复分解聚合(ROMP)，新的生物基聚合物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

The synthesis and manipulation of certain Diels–Alder adducts of levoglucosenone and iso-levoglucosenone

Diels–Alder cycloaddition reactions between the biomass-derived platform molecule levoglucosenone (2) and various cyclic dienes such as α-terpinene produced a range of adducts, including compound 28. Manipulation of these adducts then afforded a series of derivatives. So, for example, reductions of the associated carbonyl groups delivered the corresponding alcohols including compound 29 and on reaction of these with diethylaminosulfur trifluoride rearranged fluorination products such as tetracycle 30 were obtained. An analogous suite of compounds was obtained by manipulation of the Diels–Alder adducts derived from reacting the same dienes with iso-levoglucosenone that was itself obtained through simple manipulation of levoglucosenone. Our earlier studies suggest that various of these derivatives could be used in the production, via ring-opening metathesis polymerisation (ROMP), of new bio-based polymers.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Australian Journal of Chemistry 化学-化学综合

CiteScore

2.50

自引率

0.00%

发文量

审稿时长

1.3 months

期刊介绍： Australian Journal of Chemistry - an International Journal for Chemical Science publishes research papers from all fields of chemical science. Papers that are multidisciplinary or address new or emerging areas of chemistry are particularly encouraged. Thus, the scope is dynamic. It includes (but is not limited to) synthesis, structure, new materials, macromolecules and polymers, supramolecular chemistry, analytical and environmental chemistry, natural products, biological and medicinal chemistry, nanotechnology, and surface chemistry. Australian Journal of Chemistry is published with the endorsement of the Commonwealth Scientific and Industrial Research Organisation (CSIRO) and the Australian Academy of Science.