Ladderane


Ladderane

Chembox new
Name = Ladderane
ImageFile = Ladderane-2D.svg
ImageSize = 160px
ImageFile1 =
IUPACName = Ladderane
Section2 = Chembox Properties
Formula = C2n+2H2n+6"'
MolarMass =
MeltingPt =
BoilingPt =
Density =

Section8 = Chembox Related
OtherCpds = Cyclobutane
A ladderane is an organic molecule containing two or more fused rings of cyclobutane. The name is a portmanteau because the serial cyclobutane rings look like a ladder and are singly bonded like alkanes. Ladderanes, like other cyclic rings, can be formed by the reduction of a carbon-carbon double bond into a single bond, concomitant with the creation of a new carbon-carbon bond to close the ring.cite journal|author=Nouri, D H, Tantillo, D J | title=They Came from the Deep: Syntheses, Applications, and Biology of Ladderanes | journal=Curr. Org. Chem. | year=2006 | volume=10 | pages=2055–2074 | doi=10.2174/138527206778742678] cite conference|author=Nouri, D H and Tantillo, D J | title=Ladderane Formation Mechanisms: The Uphill Battle | booktitle=232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006 | pages=COMP 247]

The geometry of ladderanes is highly strained because ligands to the carbon atoms cannot extend to their ideal angles. However, examples of ladderanes have been found in living organisms. An example is "pentacycloanammoxic acid" [cite journal
journal = Nature
volume = 419
pages = 708–712
year = 2002
doi = 10.1038/nature01128
title = Linearly concatenated cyclobutane lipids form a dense bacterial membrane
author = J. S. Sinninghe Damsté, M. Strous, W. I. C. Rijpstra, E. C. Hopmans, J. A. J. Geenevasen, A. C. T. van Duin, L. A. van Niftrik and M. S. M. Jetten
] which is composed of 5 fused cyclobutane units. It is found in bacteria performing the anammoxprocess where it forms part of a tight and very dense membrane believed to protect the organism from toxic hydroxylamine and hydrazine involved in the production of nitrogen and water from nitrite ions and ammonia. [cite journal
title = Enantioselective Synthesis of Pentacycloanammoxic Acid
author = Vincent Mascitti and E. J. Corey
journal = J. Am. Chem. Soc.
year = 2006
volume = 128
issue = 10
pages = 3118
doi = 10.1021/ja058370g
]

:

References

* Henning Hopf. "Chains, rings, substituents: Tales from the marvelous edifice of modern organic chemistry." Lecture at the 234th American Chemical Society National Meeting in Boston, MA on Tuesday, August 21, 2007, 2:45 to 3:30 PM.
* [http://blueline.ucdavis.edu/2ndTier/3rdTier/Ladderanes.html Ladderane lipids website, UC Davis]

ee also

* Cyclobutane


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