Atranes are a class of tricyclic molecules with three five-membered rings. It is a heterocyclic structure similar to the

propellane In organic chemistry, propellane is any member of a class of polycyclic hydrocarbons, whose carbon skeleton consists of three rings of carbon atoms sharing a common carbon–carbon covalent bond. The concept was introduced in 1966 by D. Ginsbu ...

s. It has a

transannular In organic chemistry annulation (from the Latin ''anellus'' for "little ring"; occasionally annelation) is a chemical reaction in which a new ring is constructed on a molecule. : Examples are the Robinson annulation, Danheiser annulation and cert ...

dative bond from a nitrogen at one bridgehead to a

Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any sp ...

ic atom such as silicon or boron at the other bridgehead.Voronkov, Mikhail G.; Baryshok, Viktor P. "Atranes - a new generation of biologically active substances" (in Russian) Vestnik Rossiiskoi Akademii Nauk 2010, volume 80, 985-992. The name "atrane" was first proposed by .

Nomenclature

Various atranes are named depending on the central element, e.g. "silatrane" (E = silicon); "boratrane" (E =

boron Boron is a chemical element with the symbol B and atomic number 5. In its crystalline form it is a brittle, dark, lustrous metalloid; in its amorphous form it is a brown powder. As the lightest element of the ''boron group'' it has th ...

); "phosphatrane" (E = phosphorus), etc. It is also proposed that when Y = nitrogen, the prefix "aza" be inserted before ''element'' + "atrane" (azasilatrane, for example) because atranes wherein E = silicon and Y = oxygen have been referred to as just "silatranes".

Structure and properties

Silatranes exhibit unusual properties as well as biological activity in which the coordination of nitrogen to silane plays an important role. Some derivatives such as

phenylsilatrane Phenylsilatrane is a convulsant chemical which has been used as a rodenticide. Phenylsilatrane and some of its analogs with 4-substituents of H, CH3, Cl, Br, and CSi(CH3)3 are highly toxic to mice. They have been observed in the laboratory to inh ...

are highly toxic. The transannular coordinate bond in atranes can be stretched (quasiatranes) and even broken (proatranes,) by controlling their

stereoelectronic An electronic effect influences the structure, reactivity, or properties of molecule but is neither a traditional bond nor a steric effect. In organic chemistry, the term stereoelectronic effect is also used to emphasize the relation between t ...

properties. The strength of the transannular interaction depends on the electronegativity of the participating atoms and the size of the rings. 290 px, Protonation of Verkade base gives an atrane.

Proazaphosphatrane In chemistry, a Verkade base (or Verkade superbase) is a superbase with the formula P(MeNCH2CH2)3N. A colorless oil, it is an aminophosphine although its inventor John Verkade called it proazaphosphatrane. The trimethyl derivative or 2,5,8,9-tet ...

is a very strong non- ionic base and is utilized in various types of

organic Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or is the product ...

synthesis Synthesis or synthesize may refer to: Science Chemistry and biochemistry *Chemical synthesis, the execution of chemical reactions to form a more complex molecule from chemical precursors ** Organic synthesis, the chemical synthesis of organ ...

as an efficient catalyst. PetersFeN2-attrane

References

{{commons category, lcfirst=yes Heterocyclic compounds

Nomenclature

Structure and properties

See also

References