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One‐Pot Assembly of 7‐Methylene‐6,8‐dioxabicyclo[3.2.1]octanes, Congeners of Frontalin, from Ketones and Acetylene
Author(s) -
Trofimov Boris A.,
Schmidt Elena Yu.,
Ushakov Igor A.,
Mikhaleva Albina I.,
Zoridezhda V.,
Protsuk Nadezhda I.,
Senotrusova Elena Yu.,
Skital'tseva Elena V.,
Kazheva Olga N.,
Alexandrov Grigorii G.,
Dyachenko Oleg A.
Publication year - 2009
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.200900853
Subject(s) - chemistry , acetylene , methylene , organic chemistry , sex pheromone , molecule , medicinal chemistry , botany , biology
A facile, consecutive, self‐consisting assembly of two molecules of ketones with two molecules of acetylene to afford 7‐methylene‐6,8‐dioxabicyclo[3.2.1]octanes, which are unknown congeners of widespread insect pheromones, has been discovered. The reaction is realized in a one‐pot procedure in a MOH/DMSO system (M = K, Cs) at 80 °C for 1 h under acetylene pressure or under atmospheric pressure; the isolated yields of the bicycles reached 86 %. The new reaction conceptually contributes to the synthesis of insect pheromones as well as to the chemistry of ketones and acetylene. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)