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Sequential [3+2] Cycloaddition/Air Oxidation Reactions: Triazoloyl Ion Assisted Oxidative Cleavage of Alkynes
Author(s) -
Ponpandian Thanasekaran,
Muthusubramanian Shanmugam,
Rajagopal Sridharan
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300441
Subject(s) - chemistry , cycloaddition , oxidative cleavage , alkyne , cleavage (geology) , aldehyde , oxidative phosphorylation , sodium azide , ion , oxygen , photochemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry , geotechnical engineering , fracture (geology) , engineering
Upon treatment with sodium azide in DMF, bisalkynes undergo chemoselective [3+2] cycloaddition followed by oxidative cleavage of the other alkyne unit by atmospheric oxygen. The neighboring triazoloyl ion is found to assist the cleavage process ultimately to deliver an acid and an aldehyde.