+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Allyl, methallyl, prenyl, and methylprenyl ethers as protected alcohols: their selective cleavage with diphenyldisulfone under neutral conditions

Allyl, methallyl, prenyl, and methylprenyl ethers as protected alcohols: their selective cleavage with diphenyldisulfone under neutral conditions

Organic Letters 6(16): 2693-2696

Diphenyldisulfone is a mild and efficient reagent for selective cleavage of methylprenyl (2,3-dimethylbut-2-en-1-yl), prenyl (3-methylbut-2-en1-yl), and methallyl (2-methylallyl) ethers. These reaction conditions are compatible with the presence of other protecting groups such as acetals, acetates, and allyl, benzyl, and TBDMS ethers. Exposure of 2,3-dimethylbut-2-en-1-yl and 3-methylbut-2-en1-yl ethers to diphenyldisulfone led to the formation of 2,3-dimethylbuta-1,3-diene and isoprene, respectively. 2-Methylallyl ethers undergo isomerization to 2-methylpropenyl ethers, which are easily hydrolyzed into the corresponding free alcohols and isobutyraldehyde. [reaction: see text]

Please choose payment method:

(PDF emailed within 0-6 h: $19.90)

Accession: 048210946

Download citation: RISBibTeXText

PMID: 15281746

DOI: 10.1021/ol049135q

Related references

Remarkable Solvent Effect on Pd(0)-Catalyzed Deprotection of Allyl Ethers Using Barbituric Acid Derivatives: Application to Selective and Successive Removal of Allyl, Methallyl, and Prenyl Ethers. Synlett 2007(20): 3131-3136, 2007

Selective cleavage of allyl and propargyl ethers to alcohols catalyzed by Ti(O-i-Pr)4/MXn/Mg. Organic Letters 9(5): 773-776, 2007

Polysulfones: solid organic catalysts for the chemoselective cleavage of methyl-substituted allyl ethers under neutral conditions. Chemical Communications 2004(21): 2444-2445, 2004

Iodine in Dichloromethane - A Simple Method for Selective Cleavage of Prenyl Ethers. Synlett 2001(12): 1989-1991, 2001

Application of a new phosphorus-free palladium heterogeneous nanocatalyst supported on modified MWCNT the highly selective and efficient cleavage of propargyl, allyl, and benzyl phenol ethers under mild conditions. Molecular Diversity 19(3): 481-500, 2016

SmI2/water/amine mediates cleavage of allyl ether protected alcohols: application in carbohydrate synthesis and mechanistic considerations. Organic Letters 5(22): 4085-4088, 2003

Iridium-Catalyzed Intermolecular Asymmetric Dearomatization of β-Naphthols with Allyl Alcohols or Allyl Ethers. Angewandte Chemie 56(12): 3237-3241, 2017

Selective cleavage of the C-O bonds in alcohols and asymmetric ethers by dissociative electron attachment. Physical Chemistry Chemical Physics 11(35): 7640-7648, 2009

Pd-catalyzed nucleophilic alkylation of aliphatic aldehydes with allyl alcohols: allyl, 2-tetrahydrofuryl, and 2-tetrahydropyranyl ethers as useful C3, C4, and C5 sources. Angewandte Chemie 42(29): 3392-3395, 2003

Methylprenyl and Prenyl Protection for Sulfonamides. Synlett 26(02): 183-186, 2014

Selective Oxidation of Benzylic Alcohols and Ethers and Oxidative Cleavage of Benzylic Tetrahydropyranyl and Trimethylsilyl Ethers to Their Carbonyl Compounds by Dinitrogen TetroxideImpregnated Activated Charcoal (N 2 O 4 /Charcoal). Synthetic Communications 35(11): 1527-1533, 2005

Allyl and prenyl ethers of mansonone G, new potential semisynthetic antibacterial agents. Bioorganic and Medicinal Chemistry Letters 26(21): 5300-5303, 2016

Catecholborane Reductive Cleavage of Allyl and Propargyl Acetals and Ketals: A Simple Route to Allyl and Prop-2-ynyl Ethers. Synthetic Communications 21(7): 907-913, 1991

Silane/iodine-based cleavage of esters and ethers under neutral conditions. Proceedings of the National Academy of Sciences of the United States of America 75(1): 4-6, 1978

Influence of hydrogen bonding in the activation of nucleophiles: PhSH-(catalytic) KF in N-methyl-2-pyrrolidone as an efficient protocol for selective cleavage of alkyl/aryl esters and aryl alkyl ethers under nonhydrolytic and neutral conditions. Journal of Organic Chemistry 67(8): 2541-2547, 2002