Triangulane

A triangulane is a hydrocarbon consisting of a series of spiro-linked cyclopropane rings. The systematic naming pattern for these molecules is "[n]triangulane", where n is the number of cyclopropane units.

[2]Triangulane, the simplest triangulane compound, consists of a chain of two spiro-linked cyclopropane rings

The simplest such chemical, [2]triangulane by the systematic nomenclature of this class, is named spiro[2.2]pentane by standard spirocyclic structure nomenclature. Chains consisting of four or more cyclopropane units—[4]triangulane and higher—can form chiral helices.[1] This property is unusual for a molecule that contains no stereogenic atoms; the chiral nature is due to restricted mobility of the chain ends analogous to helicene molecules.

The rings can form a branched or cyclic patterns. For example, [3]rotane is a branched [4]triangulane; it consists of one additional cyclopropane attached to the central ring of a [3]triangulane chain.[2]

References

Zefirov, Nikolai S.; Kozhushkov, Serge I.; Kuznetsova, T. S.; Kokoreva, O. V.; Lukin, K. A.; Ugrak, B. I.; Tratch, Serge S. (1990). "Triangulanes: stereoisomerism and general method of synthesis". J. Am. Chem. Soc. 112 (21): 7702–7707. doi:10.1021/ja00177a034.
de Meijere, Armin; Kozhushkov, Sergei I.; Fokin, Andrey A.; Emme, Ingo; Redlich, Stefan; Schreiner, Peter R. (2003). "New structurally interesting cyclopropane derivatives. A world of wonders and surprises" (PDF). Pure Appl. Chem. 75 (5): 549–562. doi:10.1351/pac200375050549.

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[1] Zefirov, Nikolai S.; Kozhushkov, Serge I.; Kuznetsova, T. S.; Kokoreva, O. V.; Lukin, K. A.; Ugrak, B. I.; Tratch, Serge S. (1990). "Triangulanes: stereoisomerism and general method of synthesis". J. Am. Chem. Soc. 112 (21): 7702–7707. doi:10.1021/ja00177a034.

[2] Meijere, Armin; Kozhushkov, Sergei I.; Fokin, Andrey A.; Emme, Ingo; Redlich, Stefan; Schreiner, Peter R. (2003). "New structurally interesting cyclopropane derivatives. A world of wonders and surprises" (PDF). Pure Appl. Chem. 75 (5): 549–562. doi:10.1351/pac200375050549.