Derek H.R. Barton

Bio: Derek H.R. Barton is an academic researcher from Texas A&M University. The author has contributed to research in topics: Radical & Decarboxylation. The author has an hindex of 37, co-authored 153 publications receiving 5249 citations. Previous affiliations of Derek H.R. Barton include Institut de Chimie des Substances Naturelles & Centre national de la recherche scientifique.

A new method for the deoxygenation of secondary alcohols

Abstract: On reaction with tributylstannane, O-cycloalkyl thiobenzoates and O-cycloalkyl S-methyl dithiocarbonates, derived from secondary alcohols, give good yields of the corresponding hydrocarbons. The mechanism of this planned reaction is radical in character and thus rearrangements common in carbocation reactions are avoided. The particular applicability of this procedure in sugar chemistry is illustrated. The reaction takes place under neutral conditions compatible with the presence of the functional groups which normally occur in aminoglycoside antibiotics.A convenient general synthesis of O-cycloalkyl thioesters has been developed which gives access to O-cycloalkyl thioformates and thioacetates. An extension of this method affords the hitherto unknown O-cycloalkyl seleno-formates and selenobenzoates. An attempted extension of the method to the synthesis of O-chloesteryl tellurobenzoate gave, unexpectedly, a good yield of benzyl cholesteryl ether.

New and improved methods for the radical decarboxylation of acids

Abstract: Carboxylic acid esters derived from N-hydroxypyridine-2-thione undergo efficient radical chain decarboxylation to the corresponding nor-alkane on treatment with either tri-n-butylstannane or t-butylmercaptan; in the absence of these hydrogen atom donors a smooth decarboxylative rearrangement giving noralkyl 2-pyridyl sulphides is observed.

Living radical polymerization by the RAFT process

Abstract: This paper presents a review of living radical polymerization achieved with thiocarbonylthio compounds [ZC(=S)SR] by a mechanism of reversible addition–fragmentation chain transfer (RAFT). Since we first introduced the technique in 1998, the number of papers and patents on the RAFT process has increased exponentially as the technique has proved to be one of the most versatile for the provision of polymers of well defined architecture. The factors influencing the effectiveness of RAFT agents and outcome of RAFT polymerization are detailed. With this insight, guidelines are presented on how to conduct RAFT and choose RAFT agents to achieve particular structures. A survey is provided of the current scope and applications of the RAFT process in the synthesis of well defined homo-, gradient, diblock, triblock, and star polymers, as well as more complex architectures including microgels and polymer brushes.