Standard Article

Organomanganese-Mediated Radical Reactions

Organomanganese Compounds (2011)

  1. Gregory K. Friestad

Published Online: 15 SEP 2010

DOI: 10.1002/9780470682531.pat0532

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Friestad, G. K. 2010. Organomanganese-Mediated Radical Reactions. Patai's Chemistry of Functional Groups. .

Author Information

  1. University of Iowa, Department of Chemistry, Iowa City, Iowa 52 242, USA

Publication History

  1. Published Online: 15 SEP 2010

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

Free radical reactions offer functional group compatibility which complements that of carbanion reagents. A variety of synthetically useful transformations proceeding via free radicals, including reductions, carbonylations, reductive additions, cyclizations and polymerizations, may be induced by organomanganese reagents. These generate carbon-centered radicals from organic halides; photolysis with dimanganese decacarbonyl leads to halogen atom abstraction, or triorganomanganate reagents effect electron transfer followed by loss of halide ion. Synthetic methods employing these reagents are reviewed, with emphasis on carbon-carbon bond construction, stereoselectivity, and applications in natural product synthesis. Reductive dehalogenation, Wurtz coupling, intermolecular radical additions and carbonylations, radical cyclizations including atom transfer methods, and radical addition to imino compounds are discussed in the context of recent developments using organomanganese reagents.

Keywords:

  • reduction;
  • radical addition;
  • cyclization;
  • carbonylation;
  • amine synthesis;
  • imines;
  • hydrazones;
  • stereoselectivity

Featured Compounds

VIEW

  1. 1 - 61
Compound 1
Molecular Weight:389.9771
Molecular Formula:C10Mn2O10
InChIKey:QFEOTYVTTQCYAZ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound 2
Molecular Weight:353.918
Molecular Formula:C14H10Fe2O4
InChIKey:MEIBNUPMCHZODC-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound A
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound B
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 3a
Molecular Weight:177.1998
Molecular Formula:C10H11NO2
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 3b
Molecular Weight:253.2958
Molecular Formula:C16H15NO2
InChIKey:QEOCTJMBYZNEJH-CQSZACIVSA-N
View compound in article | Full details | Search for this compound
Compound 3c
Molecular Weight:129.157
Molecular Formula:C6H11NO2
InChIKey:YBUPWRYTXGAWJX-RXMQYKEDSA-N
View compound in article | Full details | Search for this compound
Compound 3d
Molecular Weight:163.1733
Molecular Formula:C9H9NO2
InChIKey:QDMNNMIOWVJVLY-MRVPVSSYSA-N
View compound in article | Full details | Search for this compound
Compound 3e
Molecular Weight:175.184
Molecular Formula:C10H9NO2
InChIKey:XWZLNPUWNUTPAU-BDAKNGLRSA-N
View compound in article | Full details | Search for this compound
Compound 4a
Molecular Weight:192.2145
Molecular Formula:C10H12N2O2
InChIKey:VGOMGOOWGTZCRK-VIFPVBQESA-N
View compound in article | Full details | Search for this compound
Compound 4b
Molecular Weight:268.3104
Molecular Formula:C16H16N2O2
InChIKey:PIMMVNXBENEFFO-CQSZACIVSA-N
View compound in article | Full details | Search for this compound
Compound 4c
Molecular Weight:144.1717
Molecular Formula:C6H12N2O2
InChIKey:HORXQDKUJVWRKN-RXMQYKEDSA-N
View compound in article | Full details | Search for this compound
Compound 4d
Molecular Weight:178.1879
Molecular Formula:C9H10N2O2
InChIKey:QJVCROYSDBKBPH-MRVPVSSYSA-N
View compound in article | Full details | Search for this compound
Compound 4e
Molecular Weight:190.1986
Molecular Formula:C10H10N2O2
InChIKey:MECFKICKTWZJDD-BDAKNGLRSA-N
View compound in article | Full details | Search for this compound
Compound 5
Molecular Weight:232.2783
Molecular Formula:C13H16N2O2
InChIKey:LQOPQDUYISKTEZ-ACLQVGRQSA-N
View compound in article | Full details | Search for this compound
Compound 6
Molecular Weight:280.3211
Molecular Formula:C17H16N2O2
InChIKey:DSZCWUHTPCBTIP-IQFISFIMSA-N
View compound in article | Full details | Search for this compound
Compound 7
Molecular Weight:230.2625
Molecular Formula:C13H14N2O2
InChIKey:HJVDFZOMIFCGFR-INGDVHDHSA-N
View compound in article | Full details | Search for this compound
Compound 8
Molecular Weight:252.697
Molecular Formula:C12H13ClN2O2
InChIKey:ULHTWADCRXLOIP-NGPAHMQLSA-N
View compound in article | Full details | Search for this compound
Compound 9
Molecular Weight:280.75
Molecular Formula:C14H17ClN2O2
InChIKey:RUCKDBXSWKYRSC-WFSQQTBHSA-N
View compound in article | Full details | Search for this compound
Compound 10
Molecular Weight:294.777
Molecular Formula:C15H19ClN2O2
InChIKey:MAMWRUWWKMMQNG-FBJMNJBLSA-N
View compound in article | Full details | Search for this compound
Compound 11
Molecular Weight:348.512
Molecular Formula:C18H28N2O3Si
InChIKey:GQIGXCMMRHTKPF-ZVCOJXFSSA-N
View compound in article | Full details | Search for this compound
Compound 12
Molecular Weight:346.851
Molecular Formula:C19H23ClN2O2
InChIKey:SOEVZRFSQBYICF-YOTKJTIDSA-N
View compound in article | Full details | Search for this compound
Compound 13
Molecular Weight:442.6663
Molecular Formula:C25H38N2O3Si
InChIKey:MZODVYXQGHRWLL-GCRRVMKWSA-N
View compound in article | Full details | Search for this compound
Compound 14
Molecular Weight:482.6871
Molecular Formula:C27H38N2O4Si
InChIKey:WFVMRGHQGNMFKG-CGVHKBLPSA-N
View compound in article | Full details | Search for this compound
Compound 15
Molecular Weight:396.4364
Molecular Formula:C22H24N2O5
InChIKey:JKCJMYGYYGIFQM-UDJWRJMGSA-N
View compound in article | Full details | Search for this compound
Compound 16
Molecular Weight:375.4204
Molecular Formula:C22H21N3O3
InChIKey:JQIFBRQVWRUUGF-AMAFCZHPSA-N
View compound in article | Full details | Search for this compound
Compound 3
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 4
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 17
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 18
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 22
Molecular Weight:288.3847
Molecular Formula:C17H24N2O2
InChIKey:GCAZSQXYVLERCQ-ZWPWWNDZSA-N
View compound in article | Full details | Search for this compound
Compound 26
Molecular Weight:336.4275
Molecular Formula:C21H24N2O2
InChIKey:KEELRPRWIWRXGP-LOFJQREMSA-N
View compound in article | Full details | Search for this compound
Compound (E)-27
Molecular Weight:276.2878
Molecular Formula:C14H16N2O4
InChIKey:HJFCRYCBFOQVPP-XBUHWIKASA-N
View compound in article | Full details | Search for this compound
Compound (Z)-27
Molecular Weight:276.2878
Molecular Formula:C14H16N2O4
InChIKey:HJFCRYCBFOQVPP-GQVHDAKQSA-N
View compound in article | Full details | Search for this compound
Compound 19
Molecular Weight:274.3581
Molecular Formula:C16H22N2O2
InChIKey:OPDKBSUDCVUYLL-AQTLKONXSA-N
View compound in article | Full details | Search for this compound
Compound 20
Molecular Weight:300.3954
Molecular Formula:C18H24N2O2
InChIKey:HUNVGSBTVDLHJH-QBHGPPCGSA-N
View compound in article | Full details | Search for this compound
Compound 21
Molecular Weight:314.4219
Molecular Formula:C19H26N2O2
InChIKey:HFDHAEVXMWCUGY-DMEQXSTQSA-N
View compound in article | Full details | Search for this compound
Compound 23
Molecular Weight:322.4009
Molecular Formula:C20H22N2O2
InChIKey:MVZOGCFALMIGNY-GRNWLOBZSA-N
View compound in article | Full details | Search for this compound
Compound 24
Molecular Weight:348.4382
Molecular Formula:C22H24N2O2
InChIKey:KYAANULTJVVVLO-SSRRSSPNSA-N
View compound in article | Full details | Search for this compound
Compound 25
Molecular Weight:362.4647
Molecular Formula:C23H26N2O2
InChIKey:GKBDJGMQONQJIR-WZFMIUBLSA-N
View compound in article | Full details | Search for this compound
Compound C
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound D
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound E
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 2a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 28
Molecular Weight:466.3525
Molecular Formula:C22H27IO3
InChIKey:NLFOEUFHIMGOLS-FNAHDJPLSA-N
View compound in article | Full details | Search for this compound
Compound 29
Molecular Weight:688.9679
Molecular Formula:C40H56N2O6Si
InChIKey:BAKVRMFWXFFAQJ-FQDXYEBNSA-N
View compound in article | Full details | Search for this compound
Compound 30
Molecular Weight:670.9527
Molecular Formula:C40H54N2O5Si
InChIKey:PUKQKQRTLLWTSD-FQDXYEBNSA-N
View compound in article | Full details | Search for this compound
Compound 31
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 32
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound 33
Molecular Weight:294.3477
Molecular Formula:C18H18N2O2
InChIKey:NRSXBQPCPNPGGT-MIQLPHMESA-N
View compound in article | Full details | Search for this compound
Compound 34a
Molecular Weight:314.279
Molecular Formula:C10H23IOSi
InChIKey:URLWDCDRHNATBW-VIFPVBQESA-N
View compound in article | Full details | Search for this compound
Compound 35a
Molecular Weight:482.7302
Molecular Formula:C28H42N2O3Si
InChIKey:MESVAVMQCXFSQA-HDYLNDSGSA-N
View compound in article | Full details | Search for this compound
Compound 34b
Molecular Weight:200.0181
Molecular Formula:C4H9IO
InChIKey:DTINAOLTRPNYET-BYPYZUCNSA-N
View compound in article | Full details | Search for this compound
Compound 35b
Molecular Weight:368.4693
Molecular Formula:C22H28N2O3
InChIKey:CTROWBIKTMLHSS-IOMROCGXSA-N
View compound in article | Full details | Search for this compound
Compound 36
Molecular Weight:482.6871
Molecular Formula:C27H38N2O4Si
InChIKey:WFVMRGHQGNMFKG-CGVHKBLPSA-N
View compound in article | Full details | Search for this compound
Compound 37
Molecular Weight:526.7827
Molecular Formula:C30H46N2O4Si
InChIKey:MTGAXJGLNRPYBF-UPRLRBBYSA-N
View compound in article | Full details | Search for this compound
Compound 38
Molecular Weight:334.41
Molecular Formula:C18H26N2O4
InChIKey:QPLZOGQNYPCOMA-JKSUJKDBSA-N
View compound in article | Full details | Search for this compound
Compound 39
Molecular Weight:255.2341
Molecular Formula:C10H16F3NO3
InChIKey:BGWBOEYZNZNZRQ-SSDOTTSWSA-N
View compound in article | Full details | Search for this compound
Compound 40a
Molecular Weight:306.3569
Molecular Formula:C16H22N2O4
InChIKey:KFOCNEANJWCUCG-BBRMVZONSA-N
View compound in article | Full details | Search for this compound
Compound 40b
Molecular Weight:320.3835
Molecular Formula:C17H24N2O4
InChIKey:HYDRIIPXHUDEAA-YOEHRIQHSA-N
View compound in article | Full details | Search for this compound
Compound 41
Molecular Weight:249.3056
Molecular Formula:C14H19NO3
InChIKey:BHAMWDQOWGPOAQ-AWEZNQCLSA-N
View compound in article | Full details | Search for this compound

VIEW

  1. 1 - 61