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The Preparation and Structures of Several Cross‐Conjugated Allenes (“Allenic Dendralenes”)
Author(s) -
Lehrich Friedhelm,
Hopf Henning,
Grunenberg Jörg
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001508
Subject(s) - isomerization , chemistry , conjugated system , allene , derivative (finance) , organic chemistry , base (topology) , catalysis , polymer , mathematical analysis , mathematics , financial economics , economics
Abstract The cross‐conjugated allenes (“allenic dendralenes”) 2‐allenylbuta‐1,3‐diene ( 2 ), 1,1‐divinylallene ( 3 , prepared here as the methyl derivative 49 ), and 1,1‐diallenylethene ( 4 ) are prepared either by S N 2′‐substitution processes from appropriate allenic or acetylenic precursors or by base‐catalyzed isomerizations of propargylic substrates. Thermal elimination/isomerization routes to these highly unsaturated hydrocarbons require reaction conditions under which these allenes undergo secondary transformations. The new oligoolefins, the structures of which have been calculated by MP2 methods, are interesting substrates for addition and isomerization reactions.