The xanthate route to tetralones, tetralins, and naphthalenes. A brief account

Abstract

The present account summarises routes to tetralones, tetralines, and naphthalenes based on the chemistry of xanthates developed in the authors’ laboratory. The degenerative reversible transfer of xanthates allows radical addition...

Some Aspects of α-(Acyloxy)alkyl Radicals in Organic Synthesis

“…The ability to access 4-acyloxytetralones by radical addition of phenacyl xanthates to vinyl esters followed by ring closure onto the aromatic ring opens up another synthetic application, namely the synthesis of naphthalenes by acid-catalyzed elimination of the acyloxy group. This approach is illustrated by the examples in Scheme 13 [48][49][50]. The addition and cyclization are performed in the same flask since both steps use DLP as both the initiator and stoichiometric oxidant.…”

Direct C−H Sulfuration: Synthesis of Disulfides, Dithiocarbamates, Xanthates, Thiocarbamates and Thiocarbonates

“…Although there are some elegant reviews regarding the synthesis of thioethers, [99] sulfones, [100] trifluoromethyl thioethers [101] and thiocyanates [102] via direct C−H sulfuration, there is no comprehensive review focusing on the direct C−H disulfuration, dithiocarbamation, xanthylation, thiocarbamation and thiocarbonation, despite remarkable progress in these fields. Moreover, there are only a few recent reviews regarding the applications of organic dithiocarbamates [13c–e] and xanthates [14m,o,r] . Given the diverse biological activities and wide applications of organic disulfides, dithiocarbamates, xanthates, thiocarbamates and thiocarbonates, and the lack of systematic reviews for the preparation of such compounds, this review aims to provide a critical overview of the progress made in the direct C−H sulfuration for synthesizing these compounds (until Jan 2024), with a special emphasis on elucidating substrate scopes and mechanistic scenarios.…”

Photo-hydroacylation: 1-tetralones from ortho-allylbenzaldehydes

“…E-mail: koert@chemie.uni-marburg.de cyclopropanols, 12 the rhodium-catalysed reaction of 1-(2haloaryl)cyclobutanols 13 and the use of xanthates as precursor molecules. 14…”

“…11 Recent examples of the synthesis of substituted tetralones include the photoredox-mediated ring expansion of cyclopropanols, 12 the rhodium-catalysed reaction of 1-(2-haloaryl)cyclobutanols 13 and the use of xanthates as precursor molecules. 14…”