Identification of a Boron-Containing Intermediate in the Boron Tribromide Mediated Aryl Propargyl Ether Cleavage Reaction

An alternate reaction mechanism for the boron tribromide mediated deprotection of aryl propargyl ethers based on the isolation of a key boron-containing byproduct is proposed. On the basis of the new mechanistic insight, we discovered that HBBr2·SMe2 can also be used for cleaving aryl propargyl ethe...

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Bibliographic Details
Published in:	Journal of organic chemistry Vol. 74; no. 3; pp. 1385 - 1387
Main Authors:	Yao, Min-Liang, Reddy, Marepally Srinivasa, Zeng, Wenbin, Hall, Kelly, Walfish, Ingrid, Kabalka, George W
Format:	Journal Article
Language:	English
Published:	Washington, DC American Chemical Society 06-02-2009
Subjects:	Aliphatic compounds Alkenes - chemical synthesis Alkynes - chemistry Boron Compounds - chemical synthesis Boron Compounds - chemistry Bromides - chemistry Chemistry Ethers - chemistry Exact sciences and technology Hydrocarbons, Brominated - chemical synthesis Kinetics and mechanisms Noncondensed benzenic compounds Organic chemistry Preparations and properties Reactivity and mechanisms Vinyl Compounds - chemical synthesis Acetylenic compound Ether Deprotection Propargylic compound Reaction mechanism Phenols Organic boron compounds Cleavage Aromatic compound Ethylenic compound
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Summary:	An alternate reaction mechanism for the boron tribromide mediated deprotection of aryl propargyl ethers based on the isolation of a key boron-containing byproduct is proposed. On the basis of the new mechanistic insight, we discovered that HBBr2·SMe2 can also be used for cleaving aryl propargyl ethers.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo802207y