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1,3-Bishomocubane -> Brendane Rearrangement: Molecular Structure and Reactions of exo-2-Methanesulphonoxy-endo-9-cyanobrend-4-ene
Mehta, Goverdhan,Pandey, Paras N.,Usha, R.,Venkatesan, K.
, p. 177 - 185 (2007/10/02)
A novel one-step rearrangement of pentacyclo2,5.03,9.04,8>decan-6-one (1,3-bishomocubanone, 1) to exo-2-methanesulphonoxy-9-cyanobrend-4-ene (2a) in the presence of sodium azide in methanesulphonic acid is reported.Structure of 2a is deduced through its interesting transformations to 2-cyanodeltacyclene (13) and 2-cyanonorsnoutane (15).When the rearrangement of 1 is carried out with sodium azide in trifluoroacetic acid, 3-substituted tetracyclo2,9.04,8>nonane is also obtained in addition to brend-4-ene derivative (2b).Plausible mechanism for the formation of 2a from 1 has been proposed.Single crystal X-ray crystallographic studies on 3,5-dinitrobenzoate of exo-2-hydroxy-9-cyanobrend-4-ene (2c) have been carried out to provide unambiguous proof for the structure, and its molecular structure is discussed in detail.
