Английская Википедия:Cyclopentyne

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Шаблон:Chembox Cyclopentyne is a cycloalkyne containing five carbon atoms in the ring. Due to the ideal bond angle of 180° at each atom of the alkyne but the structural requirement that the bonds form a ring, this chemical is a highly strained structure, and the triple bond is highly reactive. The triple bond easily undergoes both [2+2] and [4+2] cycloaddition reactions.[1] Unlike benzyne, which undergoes a [2+2] addition with loss of stereochemistry at the alkene partner, cyclopentyne reacts with alkenes with retention of geometry of the partner,[2] an example of the relevance of orbital symmetry even for highly reactive structures.[3] The structure can also form a π complex with lithium cations, which affects the cycloaddition reactivity.[1] It can even interact strongly enough with copper species to form a novel type of metallacycle.[4]

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