Wieland-Miescher ketone analogues are prepared by monoalkylation of cyclohexane-1,3-dione with bromomethylcycloalkenyl bromides followed by annulation with methyl vinyl ketone; they undergo 5-exo-trig competitive intramolecular radical addition to the keto and enone olefins to give angularly fused carbocycles and propellanes, respectively.

Kalapattukuppuswamy Kuppuswamy B. Balasubramanian

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Intramolecular competitive addition of vinyl radicals to keto and alkenyl groups in Wieland–Miescher ketones—synthesis of carbocycles and propellanes

Journal of the Chemical Society, Chemical Communications

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. © 1994.

Tetrahedron Letters

An unusual radical fragmentation of 8a-cycloalkenylmethyl Wieland-Miescher ketones mediated by tri-n-butyltin hydride

Enolate alkylation of bicyclo(2.2.2)oct-5-en-2-one and radical cyclisation - a potential approach for the construction of tricyclic carbocycles

Synthetic Communications

Alkylation of cyclic 1, 3-diketones

Tetrahedron

Tandem transannular radical cyclizations. Total syntheses of (±)-modhephene and (±)-epi-modhephene

J. Chem. Soc., Chem. Commun.

trans Ring-fused bicyclic structures by 6-exo-trigonal radical closure: use of the triethylborane–stannane–air system for intramolecular radical addition to aldehydes

A tandem radical macrocyclisation - radical transannulation strategy to the taxane ring system

Intramolecular competitive addition of vinyl radicals to keto and alkenyl groups in Wieland-Miescher ketones - Synthesis of carbocycles and propellanes

Journal	Journal of the Chemical Society, Chemical Communications
ISSN	00224936
Open Access	No