Spiroheptane refers to spirocyclic hydrocarbons with the formula C(CH2)6. The parent symmetrical member of this group of compounds is spiro[3.3]heptane, which features a pair of cyclobutane rings sharing one carbon. The parent unsymmetrical member is spiro[2.4]heptane, which features cyclopropyl and cyclopentyl rings sharing one carbon.
An early example of a spiro[3.3]heptane is the dicarboxylic acid C[(CH2)2CH(CO2H)]2, also called Fecht's acid in honor of the person who obtained this compound. His route involved alkylation of malonic esters with the tetrabromide of pentaerythritol, a method modeled after the work on spiropentane.[1] [2][3]
References
edit- ^ Gustavson, G. (1896). "Ueber Aethylidentrimethylen". Journal für Praktische Chemie. 54 (1): 104–107. doi:10.1002/prac.18960540106. ISSN 0021-8383.
- ^ Fecht, H. (1907). "Über Spirocyclane". Berichte der Deutschen Chemischen Gesellschaft. 40 (3): 3883–3891. doi:10.1002/cber.190704003194.
- ^ Hulshof, L. A.; Vos, Aafje; Wynberg, Hans (1972). "Crystal and molecular structure and absolute configuration of d-sprio[3.3]heptane-2,6-dicarboxylic acid at -160.deg". The Journal of Organic Chemistry. 37 (11): 1767–1770. doi:10.1021/jo00976a022.