NDLI: Chemistry of magnesium alkyls supported by 1,5,9-trimesityldipyrromethene and 2-[(2,6-diisopropylphenyl)amino]-4-[(2,6-diisopropylphenyl)imino]pent-2-ene. A comparative study

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Chemistry of magnesium alkyls supported by 1,5,9-trimesityldipyrromethene and 2-[(2,6-diisopropylphenyl)amino]-4-[(2,6-diisopropylphenyl)imino]pent-2-ene. A comparative study

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Chemical Science Vol - 3 Issue - 9

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Chemistry of magnesium alkyls supported by 1,5,9-trimesityldipyrromethene and 2-[(2,6-diisopropylphenyl)amino]-4-[(2,6-diisopropylphenyl)imino]pent-2-ene. A comparative study

Content Provider	Royal Society of Chemistry (RSC)
Author	Choojun, Kittisak Wambua, Pasco M. Gallucci, Judith C. Chisholm, Malcolm H.
Copyright Year	2012
Abstract	The compounds LMgBun(THF) and L′MgBun(THF) where L = 1,5,9-trimesityldipyrromethene and L′ = 2-[(2,6-diisopropylphenyl)amino]-4-[(2,6-diisopropylphenyl)imino]pent-2-ene have been prepared from reactions between MgBun2 and the protonated ligands LH and L′H, respectively. Single crystal X-ray crystallographic studies reveal that in each compound the Mg2+ ion is in a distorted tetrahedral environment and further that the ligand L is more sterically demanding with respect to access to the Mg–Bun group. Related alkyl complexes (R = Me, Et, Prn, Pri, n-hexyl and CH2CH2Ph) were prepared from reactions involving LLi(THF) or L′Li(THF) and the appropriate RMgX (X = Cl or Br) and characterized by 1H NMR spectroscopy. Those where R = CH2CH2X (X = alkyl or phenyl) have characteristic α-CH2 proton resonances which are the part of an AA′XX′ pattern. Reactions with alcohols ROH (1 equiv.) give the kinetic products LMg(OR)(THF) and L′Mg(OR)(THF) which are isolable and kinetically persistent when R = a bulky group such as But and the structure of LMg(OBut)(THF) is reported and compared with that of the known compound L′Mg(OBut)(THF). With less bulky groups the compounds are labile toward ligand scrambling and the compound L′MgBun(THF) reacts with alcohols (2 equiv.) to give L′H and Mg(OR)2. Reactions with amines and carbon dioxide are described which indicate the greater reactivity of the Mg–Bun group relative to both the L′ and L ligand. With PhCHO, Ph2CO and cyclohexanone both LMgBun(THF) and L′MgBun(THF) react via β-hydrogen atom transfer to generate the appropriate alkoxide with the elimination of 1-butene. Similarly L-lactide reacts by β-H transfer to give poly-L-lactide (P-L-LA) and 1-butene while rac-lactide yields atactic polylactide in toluene–dichloromethane solutions but in the presence of ≥10 equiv. of THF, heterotactic PLA is formed. The ring-opening polymerization of ε-caprolactone also is initiated by β-H transfer and is about ten times faster than for lactide; kp(LA) = 10.7 M−1 s−1vs. kp(CL) = 110 M−1 s−1. Interestingly, the presence of lactide completely suppresses the polymerization of ε-caprolactone.
Starting Page	3445
Ending Page	3457
Page Count	13
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	3
Issue Number	12
Journal	Chemical Science
DOI	10.1039/c2sc21017g
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Caprolactone PLA Ligand Hydrogen Pri Ring of Honor Carbon dioxide Ring-opening polymerization Prn X-ray crystallography THF Cyclohexanone Alkyl Alkoxide Scrambler Tacticity Benzaldehyde Polymerization Ion Nuclear magnetic resonance spectroscopy Phenyl group Lactide Single crystal 1-Butene LA Los Angeles
Content Type	Text
Resource Type	Article
Subject	Chemistry

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Chemistry of magnesium alkyls supported by 1,5,9-trimesityldipyrromethene and 2-[(2,6-diisopropylphenyl)amino]-4-[(2,6-diisopropylphenyl)imino]pent-2-ene. A comparative study

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