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J Org Chem

Title:		"A formal, one-pot beta-chlorination of primary alcohols and its utilization in the transformation of terpene feedstock and the synthesis of a C2-symmetrical terminal bis-epoxide"
Author(s):		Swatschek J; Grothues L; Bauer JO; Strohmann C; Christmann M;
Address:		"Institute of Chemistry and Biochemistry, Organic Chemistry, Freie Universitat Berlin , Takustrasse 3, 14195 Berlin, Germany"
Journal Title:		J Org Chem
Year:		2014
Volume:		20140128
Issue:		3
Page Number:		976 - 983
DOI:		10.1021/jo402422b
ISSN/ISBN:		1520-6904 (Electronic) 0022-3263 (Linking)
Abstract:		"A one-pot transformation of alkan-1-ols into 2-chloroalkan-1-ols is described. As a practical application, terpene-derived primary alcohols were converted into semiochemicals such as olfactory lactones (aerangis lactone, whisky lactone, and cognac lactone) and pheromones (cruentol and ferrugineol). Using heptane-1,7-diol as a bifunctional substrate, the corresponding bis-epoxide was synthesized by bidirectional synthesis in good yield and high enantioselectivity"
Keywords:		Alcohols/*chemistry Epoxy Compounds/*chemical synthesis/chemistry Halogenation Molecular Structure Stereoisomerism Terpenes/*chemistry;
Notes:		"MedlineSwatschek, Jorg Grothues, Lydia Bauer, Jonathan O Strohmann, Carsten Christmann, Mathias eng Research Support, Non-U.S. Gov't 2014/01/21 J Org Chem. 2014 Feb 7; 79(3):976-83. doi: 10.1021/jo402422b. Epub 2014 Jan 28"