Propargylic Substrates Research Articles

ChemInform Abstract: Reaction of Propargylic Substrates with Triorganozincates: A Novel Method for the Preparation of Allenic Zinc Reagents Associated with Carbon‐Carbon Bond Formation.

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Reaction of propargylic substrates with triorganozincates: a novel method for the preparation of allenic zinc reagents associated with carbon-carbon bond formation

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTReaction of propargylic substrates with triorganozincates: a novel method for the preparation of allenic zinc reagents associated with carbon-carbon bond formationTakeshi Katsuhira, Toshiro Harada, Keiji Maejima, Atsushi Osada, and Akira OkuCite this: J. Org. Chem. 1993, 58, 23, 6166–6168Publication Date (Print):November 1, 1993Publication History Published online1 May 2002Published inissue 1 November 1993https://doi.org/10.1021/jo00075a002RIGHTS & PERMISSIONSArticle Views249Altmetric-Citations32LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (314 KB) Get e-AlertsSupporting Info (1)»Supporting Information Supporting Information Get e-Alerts

Regio- and stereo-chemical features of the stannylcopper(I)-induced substitution in propargylic substrates

Stannylcopper(I) species, R 3SnCu and [R 3Sn] 2CuLi, preferentially convert propargylic substrates, R 1CCCR 2R 3X (X = Br, MeCO 2, MeS(O)O or MeSO 3) into allenes R 3Sn(R 1)CCCR 2R 3. Only when the group R 1 causes much greater steric hindrance than with R 2 and R 3 is the acetylenic product R 1CCCR 2SnR 3 formed. The stereochemical course of the allene formation has been studied in both the steroid and non-steroid series, and found to be mainly or exclusively anti.

Reaction of propargylic substrates with organocopper species. Synthetic aspects

Reaction of propargylic substrates with organocopper species. Synthetic aspects