24.1. 16 1,1-Bis(heteroatom-functionalized) Allenes (Update 2014)
Book
Editors: Brøndsted Nielsen, M.; Krause, N.; Marek, I.; Schaumann, E.; Wirth, T.
Title: Knowledge Updates 2014/2
Print ISBN: 9783131762412; Online ISBN: 9783131975010; Book DOI: 10.1055/b-003-125812
1st edition © 2014 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.
Type: Multivolume Edition
Abstract
This chapter updates Science of Synthesis Sections 24.1.3, 24.1.10, 24.1.14, and 24.1.15. Mono-, bis-, tris-, and tetrakis(sulfanyl-substituted) butatrienes are obtained from alkylsulfanyl- or arylsulfanyl-substituted buta-1,3-dienes in the presence of base in petroleum ether at room temperature. The treatment of 1,1,4,4-tetrakis[4-(dimethylamino)pyridin-1-ium]-2,3-dichlorobuta-1,3-diene with thiolates in dimethyl sulfoxide leads to the formation of tetrakis(sulfanyl-substituted) butatrienes. Allenylphosphonates are synthesized by the reaction of aliphatic- or aromatic-substituted propargylic alcohols and chlorophosphites in the presence of triethylamine. The reaction of 1-bromo-1-silylallenes with butyllithium and then chlorodiphenylphosphine in tetrahydrofuran gives 1,1-bis(diphenylphosphino)allenes.