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赤式和苏式-1,2-二氟环十二烷的优势构象。

The preferred conformation of erythro- and threo-1,2-difluorocyclododecanes.

机构信息

EastChem School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK.

出版信息

Beilstein J Org Chem. 2012;8:1271-8. doi: 10.3762/bjoc.8.143. Epub 2012 Aug 10.

DOI:10.3762/bjoc.8.143
PMID:23019458
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3458748/
Abstract

Cyclododecane adopts a square-like structure with corner and edge CH(2) groups. In this study erythro- and threo-1,2-difluorocyclododecanes were prepared to explore whether the two vicinal C-F bonds, with different relative configurations, preferably locate at corner/edge or edge/edge locations. Conformational analysis comparing the diastereoisomers was explored by using a combination of (19)F{(1)H} NMR spectroscopy, computational studies and, in the case of the threo isomer, X-ray structural analysis. In the lowest energy conformers for both diastereoisomers the vicinal C-F bonds are located corner/edge, rather than edge/edge. These structures avoid placing a C-F bond endo into the ring, and appear to benefit from C-CHF-C angle widening, which relaxes 1,4-H,H transannular interactions.

摘要

环十二烷呈类似方形结构，具有角状和边缘 CH(2)基团。在这项研究中，制备了赤式和苏式 1,2-二氟环十二烷，以探究两个相邻的 C-F 键，具有不同的相对构型，是否优先位于角/边缘或边缘/边缘位置。通过结合 (19)F{(1)H}NMR 光谱、计算研究，以及在苏式异构体的情况下，进行的对映异构体的构象分析，探索了两种非对映异构体的构象分析。在两种非对映异构体的最低能量构象中，相邻的 C-F 键位于角/边缘，而不是边缘/边缘。这些结构避免了将 C-F 键内置于环中，并且似乎受益于 C-CHF-C 角的加宽，这缓解了 1,4-H,H 跨环相互作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/a3e6375844b8/Beilstein_J_Org_Chem-08-1271-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/cd9da5456c01/Beilstein_J_Org_Chem-08-1271-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/213e4ead673d/Beilstein_J_Org_Chem-08-1271-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/f10cfd9487a7/Beilstein_J_Org_Chem-08-1271-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/c7beff5d2e0a/Beilstein_J_Org_Chem-08-1271-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/1d074838f9e0/Beilstein_J_Org_Chem-08-1271-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/47bff3de048a/Beilstein_J_Org_Chem-08-1271-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/a3e6375844b8/Beilstein_J_Org_Chem-08-1271-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/cd9da5456c01/Beilstein_J_Org_Chem-08-1271-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/213e4ead673d/Beilstein_J_Org_Chem-08-1271-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/f10cfd9487a7/Beilstein_J_Org_Chem-08-1271-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/c7beff5d2e0a/Beilstein_J_Org_Chem-08-1271-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/1d074838f9e0/Beilstein_J_Org_Chem-08-1271-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/47bff3de048a/Beilstein_J_Org_Chem-08-1271-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d1ab/3458748/a3e6375844b8/Beilstein_J_Org_Chem-08-1271-g007.jpg

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J Am Chem Soc. 2005 Jan 19;127(2):482-3. doi: 10.1021/ja045299q.