Seebach synthesis

Ethyl l,3-dithiane-2-carboxylate [20462-00-4] M 192.3, b 75-77 /0.2mm, 96 /0.4mm, dj 1.220, n 1.5379. Dissolve in CHCI3, wash with aqueous K2CO3, 2 x with H2O, dry over MgS04, filter, evaporate and distil. [Eliel and Hartman J Org Chem 37 505 I972 Seebach Synthesis 1 17 1969.]... 

In an extension of the procedure, thiols react with gem-dihaloalkanes (Table 4.4) to produce thioacetals [ 10,20-23] and the reaction can be employed in the Corey-Seebach synthesis of aldehydes and ketones (see ref. 24 and references cited therein), gem-Dichlorocyclopiopanes having an electron-withdrawing group at the 2-position react with thiols to produce the thioacetals [25]. In the corresponding reaction of the thiols with biomochloromethane exclusive nucleophilic substitution of the bromo group by the thiolate anion occurs to yield the chloromethyl thioethers [13, 14] (Table 4.5). 

K. Gademann, M. Ernst, D. Hoyer, D. Seebach, Synthesis and Biological Evaluation of a cyclo-/3-Tetrapeptide as a Somatostatin Analogue , Angew. Chem., Int. Ed. 1999, 38, 1223-1226. 

E. J. Corey and D. Seebach, Synthesis of 1, n-dicarbonyl derivatives using carbanions from... 

Enders Hassel Pieter Renger Seebach Synthesis 1976, 548. 

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