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具有氧化还原活性的四硫富瓦烯和二硫烯化合物来源于取代的 1,3-二硫杂环戊烯衍生物的烯丙基 1,4-二醇重排产物。

Redox-active tetrathiafulvalene and dithiolene compounds derived from allylic 1,4-diol rearrangement products of disubstituted 1,3-dithiole derivatives.

机构信息

WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK.

出版信息

Beilstein J Org Chem. 2010 Oct 21;6:1002-14. doi: 10.3762/bjoc.6.113.

DOI:10.3762/bjoc.6.113
PMID:21085502
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2981815/
Abstract

We present a series of compounds by exploiting the unusual 1,4-aryl shift observed for electron-rich 1,3-dithiole-2-thione and tetrathiafulvalene (TTF) derivatives in the presence of perchloric acid. The mechanistic features of this rearrangement are discussed since this synthetic strategy provides an alternative route for the synthesis and functionalisation of sulfur rich compounds including redox active compounds of TTFs, and a Ni dithiolene.

摘要

我们通过利用在高氯酸存在下富电子 1,3-二硫杂环戊烯-2-硫酮和四硫富瓦烯 (TTF) 衍生物中观察到的异常 1,4-芳基移位，展示了一系列化合物。讨论了这种重排的反应机理，因为这种合成策略为包括 TTFs 的氧化还原活性化合物和 Ni 二硫烯的富硫化合物的合成和功能化提供了替代途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/0986bff353dd/Beilstein_J_Org_Chem-06-1002-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/2438f6d8d578/Beilstein_J_Org_Chem-06-1002-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/ad50f2237b8f/Beilstein_J_Org_Chem-06-1002-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/89930edd0367/Beilstein_J_Org_Chem-06-1002-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/cf5947927e33/Beilstein_J_Org_Chem-06-1002-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/52cdf444eb64/Beilstein_J_Org_Chem-06-1002-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/7411f4d4c964/Beilstein_J_Org_Chem-06-1002-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/bad72a5c4996/Beilstein_J_Org_Chem-06-1002-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/02d4a1051de9/Beilstein_J_Org_Chem-06-1002-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/67e4524ba380/Beilstein_J_Org_Chem-06-1002-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/9733669d25f9/Beilstein_J_Org_Chem-06-1002-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/21944f7b14bc/Beilstein_J_Org_Chem-06-1002-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/f4f43f135552/Beilstein_J_Org_Chem-06-1002-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/0986bff353dd/Beilstein_J_Org_Chem-06-1002-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/2438f6d8d578/Beilstein_J_Org_Chem-06-1002-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/ad50f2237b8f/Beilstein_J_Org_Chem-06-1002-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/89930edd0367/Beilstein_J_Org_Chem-06-1002-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/cf5947927e33/Beilstein_J_Org_Chem-06-1002-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/52cdf444eb64/Beilstein_J_Org_Chem-06-1002-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/7411f4d4c964/Beilstein_J_Org_Chem-06-1002-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/bad72a5c4996/Beilstein_J_Org_Chem-06-1002-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/02d4a1051de9/Beilstein_J_Org_Chem-06-1002-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/67e4524ba380/Beilstein_J_Org_Chem-06-1002-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/9733669d25f9/Beilstein_J_Org_Chem-06-1002-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/21944f7b14bc/Beilstein_J_Org_Chem-06-1002-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/f4f43f135552/Beilstein_J_Org_Chem-06-1002-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c3a8/2981815/0986bff353dd/Beilstein_J_Org_Chem-06-1002-g008.jpg

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