title: The preparation of 3-substituted-1,5-dibromopentanes as precursors to heteracyclohexanes.
abstract: 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.
authors.affiliation: Organic Materials Research Group, Department of Chemistry, Vanderbilt University, Box 1822 Station B, Nashville, TN 37235, USA, phone/fax: (615) 322-3458.
authors.forename: Bryan
authors.initials: B
authors.lastname: Ringstrand
authors.forename: Martin
authors.initials: M
authors.lastname: Oltmanns
authors.forename: Jeffrey A
authors.initials: JA
authors.lastname: Batt
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Jankowiak
authors.forename: Richard P
authors.initials: RP
authors.lastname: Denicola
authors.forename: Piotr
authors.initials: P
authors.lastname: Kaszynski