ChemInform Abstract: Unprecedented Formation of Spirobicyclo(3.1.0)hexanes Through Tandem Acetylene-Addition-Michael Cyclization

Authors :: A. I. A. Broess
Hans Hamersma
Marinus B. Groen
Source :: ChemInform. 25
Publication Year :: 2010
Publisher :: Wiley, 2010.
Abstract: Reaction of 4-pentynyltriphenylphosphonium bromide 2 with oestrone methyl ether in the presence of potassium tert -butylate produced a spirobicyclo[3.1.0]hexane rather than the anticipated Wittig product. The reaction appears to be general for pinacolone-type ketones, as was demonstrated by several examples. A mechanism for this anomalous reaction is proposed.

Subjects :: Hexane
chemistry.chemical_compound
Acetylene
chemistry
Tandem
Bromide
Potassium
Wittig reaction
chemistry.chemical_element
Ether
General Medicine
Medicinal chemistry

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