136201-20-2Relevant academic research and scientific papers
Kinetic and thermodynamic control in the synthesis of tetrahydro-pyrans and -furans from 1,4-diols by stereospecific phenylsulfanyl (PhS) migration: Competition between exo and endo transition states and between [1,2] and [1,4] sulfanyl participation
Eames, Jason,Kuhnert, Nikolai,Sansbury, Francis H.,Warren, Stuart
, p. 1211 - 1214 (2007/10/03)
The factors controlling the cyclisation of 1,4-diols with PhS migration to give THPs rather than THFs are reassessed. Furthermore we provide evidence for a competition between [1,2] and [1,4] sulfanyl participation and cyclisation onto a five membered cyclic sulfonium salt.
Synthesis of cyclic ethers and allylic sulfides by rearrangement of phenylsulfanyl substituted 1,n-diols with toluene-p-sulfonic acid and with toluene-p-sulfonyl chloride
Djakovitch, Laurent,Eames, Jason,Fox, David J.,Sansbury, Francis H.,Warren, Stuart
, p. 2771 - 2782 (2007/10/03)
Rearrangement of a series of l,n-diols (n = 2 to 12), with a PhS-group adjacent to one OH group, under two sets of conditions gives single compounds in excellent yield drawn for four possible classes of products. The effect of the chain length helps in the understanding of the different cyclisation modes and the mechanism of the rearrangements. The Royal Society of Chemistry 1999.
Synthesis of tetrahydropyrans by hydroxyl participation in phenylthio migration
Sansbury, Francis H.,Warren, Stuart
, p. 3425 - 3428 (2007/10/02)
Acid-catalysed cyclisation of substituted 1,6- or 1,4-alkane diols with suitably placed phenylthio groups leads to high yields of tetrahydropyrans formed by exo or endo hydroxyl participation during phenylthio migration with inversion at both the migration origin and terminus.
