- Indium-mediated cleavage of the trityl group from protected alcohols and diols
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The reaction of primary, secondary, allylic and benzylic trityl ethers with indium powder in MeOH/NH4Cl led to reductive cleavage of the trityl-oxygen bond, affording the corresponding alcohols in good to excellent yield under very mild reaction conditions. The detritylation process could successfully be extended to mono and detritylated diols. This methodology represents a new and efficient detritylation procedure under mild reaction conditions.
- Behloul, Cherif,Chouti, Aicha,Guijarro, David,Foubelo, Francisco,Nájera, Carmen,Yus, Miguel
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p. 7937 - 7941
(2016/11/19)
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- Detritylation Procedure under Non-Acidic Conditions: Naphthalene Catalysed Reductive Cleavage of Trityl Ethers
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The reaction of primary, secondary, allylic and benzylic trityl ethers 1 with lithium powder and a catalytic amount of naphthalene led to reductive cleavage of the trityl-oxygen bond, affording the corresponding alcohols 2 in good to excellent yields under very mild reaction conditions. The detritylation process could successfully be extended to several hydroxy, alkoxy and amino functionalised trityl ethers. This methodology represents a new and efficient detritylation procedure under non-acidic reaction conditions.
- Yus, Miguel,Behloul, Cherif,Guijarro, David
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p. 2179 - 2184
(2007/10/03)
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- THE PHOTOCHEMISTRY OF METHYL GERANATE, A MODEL CHROMOPHORE FOR INSECT JUVENILE HORMONE ANALOGS
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The irradiation of methyl geranate (3) in ether using 254 nm lamps produces methyl 5-methyl-2-isopropenyl-4-hexenoate (13), 1,6,6-trimethyl-endo-5-carbomethoxybicyclo-hexane (11), methyl 2-isopropenyl-5-methylcyclopentanecarboxylate (12) and methyl (3Z)-3,7-dimethyl-3,6-octadienoate (14).Photolysis run in water or in ether in the presence of base generates two additional dienes: methyl 3-methylene-7-methyl-6-octaenoate (16) and methyl (3E)-3,7-dimethyl-3,6-octadienoate (17).The photolysis of methyl (2E, 6E)-3,7-dimethyl-2,6-nonadienoate (4a) in ether procedures all Z/E isomers, 4a - 4d.
- Freeman, Peter K.,Siggel, Lorenz,Chamberlain, Paul H.,Clapp, Gary E.
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p. 5051 - 5064
(2007/10/02)
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