1287748-19-9Relevant academic research and scientific papers
The preparation of 3-substituted-1,5-dibromo-pentanes as precursors to heteracyclohexanes
Ringstrand, Bryan,Oltmanns, Martin,Batt, Jeffrey A.,Jankowiak, Aleksandra,Denicola, Richard P.,Kaszynski, Piotr
, p. 386 - 393 (2011/06/23)
The methodology to prepare 3-substituted 1,5-dibromopentanes I and their immediate precursors, which include 3-substituted 1,5-pentanediols VII or 4-substituted tetrahydropyrans VIII, is surveyed. Such dibromides I are important intermediates in the preparation of liquid crystalline derivatives containing 6-membered heterocyclic rings. Four dibromides 1a-1d containing simple alkyl and more complex fragments at the 3-position were prepared. 3-Propyl- and 3-pentyl-pentane-1,5-diol (2a,b) were prepared starting from either glutaconate or malonate diesters, while tetrahydropyrans 3c and 3d were obtained from tetrahydro-4H-pyran-4-one. The advantages and disadvantages of each route are discussed. Dibromides 1c and 1d were used to prepare sulfonium zwitterions 11c and 11d.
