Universität zu Köln

Soicke, Arne, Slavov, Nikolay, Neudoerfl, Joerg-Martin and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2011). Metal-Free Intramolecular Carbonyl-Olefin Metathesis of ortho-Prenylaryl Ketones. Synlett (17). S. 2487 - 2491. STUTTGART: GEORG THIEME VERLAG KG. ISSN 0936-5214

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Abstract

On treatment with boron trifluoride etherate as a Lewis acid, acetophenone and benzophenone derivatives bearing a prenyl (or a related) side chain in ortho-position were shown to undergo intramolecular carbonyl-olefin metathesis, in the absence of any transition-metal catalyst. The cationic cyclization process is supposed to proceed via an oxetane intermediate, which fragments to give the cyclization product (indene or 1,2-dihydronaphthalene) and a ketone (acetone) as a stoichiometric by-product. Several substrates were shown to afford the metathesis products with up to 93% yield.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Soicke, Arne UNSPECIFIED UNSPECIFIED UNSPECIFIED Slavov, Nikolay UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-488635
DOI:	10.1055/s-0030-1260320
Journal or Publication Title:	Synlett
Number:	17
Page Range:	S. 2487 - 2491
Date:	2011
Publisher:	GEORG THIEME VERLAG KG
Place of Publication:	STUTTGART
ISSN:	0936-5214
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language RING-CLOSING METATHESIS; ORGANIC-SYNTHESIS; DIRECT CONVERSION; CATALYSTS; ETHERS; MOLYBDENUM; REAGENTS; ALKYNES; ESTERS Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/48863