MECHANISTIC ASPECTS OF CYCLIC SULPHONIUM SALT FORMATION AND HYDROLYSIS OF 1,<i>n</i>-HALO(ALKYLTHIO) ALKANES

Anklam, Elke; Aced, Gaby; Yun, Miyong

doi:10.1080/03086648808072899

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Cited by 4 publications

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“…Method A ( Scheme 2 ) is suggested for dihaloalkanes 6a (n = 3) or 6d (n = 6). In the cases of 6b and 6c (n = 4 and 5), the reaction sequence was almost disrupted because of the formation of cyclic sulfonium salts 9 and 10 [ 23 , 24 ].…”

Section: Resultsmentioning

confidence: 99%

ω-Methylsulfanylalkyl Glucosinolates: A General Synthetic Pathway

et al. 2018

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A general pathway was devised to synthesize ω-methylsulfanylalkyl glucosinolates, which represent an important class of structurally homogeneous plant secondary metabolites. The required thiofunctionalized hydroximoyl chlorides were obtained from the corresponding α,ω-nitroalkyl methylsulfide precursors, involving as the key-step, a nitronate chlorination strategy. A coupling reaction with 1-thio-beta-d-glucopyranose, followed by O-sulfation of the intermediate thiohydroximate and final deprotection of the sugar moiety afforded the target compounds.

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Section: Resultsmentioning

confidence: 99%