Methylene bridge

The methylene bridge (methanediyl group).

In organic chemistry, a methylene bridge or methanediyl group is any part of a molecule with formula -CH
2-; namely, a carbon atom bound to two hydrogen atoms and connected by single bonds to two other distinct atoms in the rest of the molecule. It is the repeating unit in the backbone of the unbranched alkanes.

A methylene bridge can also act as a bidentate ligand joining two metals in a coordination compound, such as titanium and aluminum in Tebbe's reagent.^[1]

A methylene bridge is often called methylene group or just methylene; as in "methylene chloride" (dichloromethane CH
2Cl
2). However, the term methylene group (or "methylidene") properly applies to the CH
2 group when it is connected to the rest of the molecule by a double bond, that gives it chemical properties very distinct from those of a bridging CH
2 group.

Reactions

Compounds possessing a methylene bridge located between two strong electron withdrawing groups (such as nitro, carbonyl or nitrile groups) are sometimes called active methylene compounds.^[2] Treatment of these with strong bases can form enolates or carbanions, which are often used in organic synthesis. Examples include the Knoevenagel condensation and the malonic ester synthesis.^[3]

Examples

Some examples of methylene compounds are :

• 

  Malonic acid

• 

  Acetylacetone

• 

  Malononitrile

See also

• Methyl group
• Methylene group
• Methyne

References

1. W. A. Herrmann (1982), "The methylene bridge". In Advances in Organometallic Chemistry, volume 20, pages 195-197.
2. "Active methylene compund".
3. House, Herbert O. (1972). Modern Synthetic Reactions. Menlo Park, CA.: W. A. Benjamin. ISBN 0-8053-4501-9.