The Debromination of Pentaerythrityl Bromide by Zinc. Isolation of Spiropentane¹

Chromium carbides and cyclopropenylidenes

“…Spiropentane 70,71 is still a challenging framework to assemble by organic synthetic methods such as reduction of tetrakis(1-haloalkyl)methanes 72,73 due to multiple sidereactions and isomerization. Formal "double-cyclopropanation" by a carbido moiety to alkenes has been reported in gas-phase by use of carbon vapor, 74,75 which was generated by the arc discharge, but isomerization of the resulted spiropentanes also proceeded under such harsh conditions.…”

Stereochemistry of the Primary Carbon. IV. The Decomposition of Optically Active 1-Butyl-1-d Chlorosulfite1,2

“…Ri ment of halomagnesium derivatives of halohy-drins6•7 and the reaction of zinc with 1,3-dihalides such as pentaerythrityl tetrabromide. [8][9][10] The benzilic acid rearrangement recently has been found to involve general base participation,2 equation 3, although previously hydroxide ion was considered to be the only effective base promoting the reaction. In the general equation 2, Q is an electron pair source, Y is a stable entity (e.g., Br®, :NR3) and A is carbon or a hetero atom.…”

Ab Initio Calculations on the Thermodynamic Properties of Azaspiropentanes

“…Spiropentane has been the subject of numerous experimental studies of its various properties. Spiropentane can be synthesized by debromination of pentaerythrityl bromide with zinc dust, using acetamide as a solvent . Its structure has been studied using electron diffraction, X-ray crystallography, and nuclear magnetic resonance spectroscopy (NMR) .…”

“…Spiropentane can be synthesized by debromination of pentaerythrityl bromide with zinc dust, using acetamide as a solvent. 4 Its structure has been studied using electron diffraction, 5 X-ray crystallography, 6 and nuclear magnetic resonance spectroscopy (NMR). 7 The infrared spectrum of spiropentane 8 was recorded shortly after its structure was established by the electron diffraction study.…”