High Quality Content by WIKIPEDIA articles! Cyclobutadiene is the smallest [n]-annulene an extremely unstable hydrocarbon having a lifetime shorter than five seconds in the free state. It has chemical formula C4H4 and a rectangular structure verified by infrared studies. This is in contrast to the square geometry predicted by simple Huckel theory. Though it has alternating single and double bonds, it fails Huckel's rule, because its ring has 4 ?-electrons, and 4 is not twice an odd number. Some cyclobutadiene-metal compounds are stable because the metal atom provides 2 more electrons to the system.

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