An unusual radical fragmentation of 8a-cycloalkenylmethyl Wieland-Miescher ketones mediated by tri-n-butyltin hydride
TL;DR: In this paper, a remarkable difference in chemoselectivity was noticed in reductive cyclisation of cycloalkenyl bromides, resulting in the remote generation of the bromocyclopentenyl-methyl radical by a homolytic CC bond cleavage.
About: This article is published in Tetrahedron Letters.The article was published on 1994-01-01. It has received 5 citations till now. The article focuses on the topics: Chemoselectivity & Homolysis.
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TL;DR: In this article, a new synthetic sequence that adds the elements of ketene across the termini of a 1,5-diene is described, which leads to the formation of a tricyclic dione.
14 citations
TL;DR: In this paper, free radical annulation followed by trimethylsilyl iodide-promoted ring-opening of (R)-carvone-dichloroketene adducts leads to an unusual carbon skeleton rearrangement.
8 citations
TL;DR: In this article, the condensation of α-carbanion of Fischer-type carbene complex with 2-thiomethyl-1,3-dithiolium salts gave new heterocyclic organometallic carbenes, potentially precursors of extended TTF.
8 citations
01 Jan 1998
TL;DR: The application of organotins in organic synthesis has become a major field of organom et al. lic chemistry during the last decade as mentioned in this paper and the incredible development and sophistication of known basic chemistry now allows organotin to be essential tools for the organic chemist, very often used in the preparation of natural products.
Abstract: The application of organotins in organic synthesis has become a major field of organom et al. lic chemistry during the last decade. The incredible development and sophistication of known basic chemistry now allows organotins to be essential tools for the organic chemist, very often used in the preparation of natural products.
6 citations
TL;DR: In this article, a remarkable difference in chemoselectivity was noticed in reductive cyclisation of cycloalkenyl bromides, resulting in the remote generation of the bromocyclopentenyl-methyl radical by a homolytic CC bond cleavage.
Abstract: The behaviour of tri-n-butyltin hydride in poly functional molecule like Wieland-Miescher ketones, was found to be very unusual, a remarkable difference in chemoselectivity was noticed in the reductive cyclisation of cycloalkenyl bromides, resulting in the remote generation of the bromocyclopentenyl-methyl radical by a homolytic CC bond cleavage.
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831 citations
446 citations
TL;DR: Carboncentered radicals can form bonds with electron-rich or electron-deficient alkenes, allenes, and acetylenes, as well as construct hindered carbon-carbon bonds, which contribute to the importance of such reactions in organic synthesis.
Abstract: Organic chemists have begun to use intra- and intermolecular free-radical addition reactions to develop useful synthetic transformations. Carboncentered radicals can form bonds with electron-rich or electron-deficient alkenes, allenes, and acetylenes. Radical addition reactions can also be used to construct hindered carbon-carbon bonds. These characteristics, as well as the large number of functional groups that tolerate free-radical conditions contribute to the importance of such reactions in organic synthesis.
263 citations
230 citations
TL;DR: In this paper, a double bond reduction of unsaturated conjugated ketones was achieved in excellent yields by use of sodium dithionite in a two phase benzene-water system with Adogen as phase transfer catalyst.
46 citations