Hill, E. Alexander published the artcileRing cleavage rearrangement of cyclobutylmethylboranes, Computed Properties of 20117-47-9, the publication is Journal of Organometallic Chemistry (1982), 239(2), 279-92, database is CAplus.
Boranes prepared by hydroborating methylenecyclobutane (I) with BH3-THF, 9-borabicyclo[3.3.1]nonane, and BH3-Me2S rearranged on heating at 100-160° to open chain structures. Products after oxidation were the unrearranged cyclobutylmethanol, and 4-penten-1-ol (II), 1,4-pentanediol (III) and 1,5-pentanediol (IV). II was the major product when stoichiometric alkene:BH bonds was used; III and IV were formed with excess BH3. The rate of rearrangement using BH3-Me2S at 100° in triglyme was not significantly dependent upon the initial I-BH3 ratio (3/1 or 1.15/1) or the presence of excess Me2S. However, an equivalent amount of pyridine prevented rearrangement. Rearrangement in THF using BH3-THF also occurred at comparable rates in the presence and absence of excess BH3. Little or no isomerization of the B function into the cyclobutane ring was observed A concerted 4-center mechanism requiring a vacant B orbital was suggested.
Journal of Organometallic Chemistry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Computed Properties of 20117-47-9.
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