title: Stereocomplementary syntheses of 1,ω-distannylated E,Z-isomeric conjugated trienes, tetraenes, and pentaenes.
abstract: Stereoselective syntheses of 1,6-bis(tributylstannyl)hexa-1,3,5-trienes, 1,8-bis(tributylstannyl)octa-1,3,5,7-tetraenes, and 1,10-bis(tributylstannyl)deca-1,3,5,7,9-pentaenes with various methylation patterns were achieved based on stereocomplementary C=C bond-forming reactions. All-E isomers resulted from Ramberg-Bäcklund rearrangements of distannylated diallyl-, allylpentadienyl-, or bis- (pentadienyl)sulfones. Mono-Z-configured 1,ω-bis(tributylstannyl)-1,3,5-polyenes emerged from (Sylvestre-)Julia olefinations of Bu(3)Sn-substituted enals or dienals with Bu(3)Sn-substituted allyl or pentadienyl benzothiazolylsulfones. Related Ramberg-Bäcklund approaches provided all-E-1-bromo-6-(tributylstannyl)hexa-1,3,5-triene but not all-E-1-(tetramethyldioxaborolanyl)-6-(tributylstannyl)hexa-1,3,5-triene.
authors.affiliation: Carbogen Amcis AG, Hauptstrasse 171, 4416 Bubendorf, Switzerland.
authors.forename: Jochen
authors.initials: J
authors.lastname: Burghart
authors.forename: Achim
authors.initials: A
authors.lastname: Sorg
authors.forename: Reinhard
authors.initials: R
authors.lastname: Brückner