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CyP=O·(HOO)CHR（R = 烷基）类型的氢键合二（氢过氧基）烷加合物

Hydrogen-Bonded Di(hydroperoxy)alkane Adducts of the Type CyP=O·(HOO)CHR (R = Alkyl).

作者信息

Ashirov Rahym, Todorovic Maya, Bhuvanesh Nattamai, Blümel Janet

机构信息

Department of Chemistry, Texas A&M University, College Station, TX 77842-3012, USA.

出版信息

Molecules. 2025 Jan 15;30(2):329. doi: 10.3390/molecules30020329.

DOI:10.3390/molecules30020329
PMID:39860199
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11767494/
Abstract

Five representatives of a novel type of di(hydroperoxy)alkane adducts of phosphine oxides have been synthesized and fully characterized, including their solubility in organic solvents. The phosphine oxide CyPO () has been used in combination with the corresponding aldehydes to create the adducts CyPO·(HOO)CHCH (), CyPO·(HOO)CHCHCH (), CyPO·(HOO)CH(CH)CH (), CyPO·(HOO)CH(CH)CH (), and CyPO·(HOO)CH(CH)CH (). All adducts crystallize easily and contain the peroxide and phosphine oxide hydrogen-bonded in 1:1 ratios. The single crystal X-ray structures of - and their unique features are discussed. The P NMR spectra of the adducts - show downfield-shifted signals as compared to CyPO. In the IR spectra, the ν(P=O) wavenumbers of the adducts have smaller values than the neat phosphine oxide. All spectroscopic results of - show that the P=O bond is weakened by hydrogen-bonding to the di(hydroperoxy)alkane moieties. Adduct selectively oxidizes PPh to OPPh within minutes, and nonanal is reformed in the process. The easy synthesis, handling, and administration of these stable, solid, and soluble peroxides with well-defined composition will have a positive impact on synthetic chemistry.

摘要

已经合成并全面表征了新型氧化膦二（氢过氧基）烷烃加合物的五种代表物，包括它们在有机溶剂中的溶解度。氧化膦CyPO（）已与相应的醛结合使用，以生成加合物CyPO·(HOO)CHCH（）、CyPO·(HOO)CHCHCH（）、CyPO·(HOO)CH(CH)CH（）、CyPO·(HOO)CH(CH)CH（）和CyPO·(HOO)CH(CH)CH（）。所有加合物都易于结晶，并且含有以1:1比例氢键结合的过氧化物和氧化膦。讨论了-的单晶X射线结构及其独特特征。加合物-的P NMR光谱显示，与CyPO相比，信号向低场移动。在红外光谱中，加合物的ν(P=O)波数比纯氧化膦的值小。-的所有光谱结果表明，P=O键通过与二（氢过氧基）烷烃部分形成氢键而减弱。加合物在几分钟内将PPh选择性氧化为OPPh，在此过程中会重新生成壬醛。这些具有明确组成的稳定、固体且可溶的过氧化物易于合成、处理和施用，将对合成化学产生积极影响。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/c387662615be/molecules-30-00329-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/b3b52da93745/molecules-30-00329-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/bc0c236ef5ad/molecules-30-00329-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/59cf4b6b04dc/molecules-30-00329-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/41aa3d1c9437/molecules-30-00329-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/751170eda0fc/molecules-30-00329-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/a44c79ba1403/molecules-30-00329-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/1faf683dc580/molecules-30-00329-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/be2356a74cd0/molecules-30-00329-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/c387662615be/molecules-30-00329-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/b3b52da93745/molecules-30-00329-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/bc0c236ef5ad/molecules-30-00329-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/59cf4b6b04dc/molecules-30-00329-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/41aa3d1c9437/molecules-30-00329-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/751170eda0fc/molecules-30-00329-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/a44c79ba1403/molecules-30-00329-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/1faf683dc580/molecules-30-00329-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/be2356a74cd0/molecules-30-00329-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/11767494/c387662615be/molecules-30-00329-g009.jpg

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J Org Chem. 2020 Nov 6;85(21):14121-14138. doi: 10.1021/acs.joc.0c02180. Epub 2020 Oct 27.
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