cyclopropanation
Sign in to saveIn organic chemistry, cyclopropanation refers to any chemical process which generates cyclopropane () rings. It is an important process in modern chemistry as many useful compounds bear this motif; for example pyrethroid insecticides and a number of quinolone antibiotics (ciprofloxacin, sparfloxacin, etc.). However, the high ring strain present in cyclopropanes makes them challenging to produce and generally requires the use of highly reactive species, such as carbenes, ylids and carbanions. Many of the reactions proceed in a cheletropic manner.
~7 min read
Encyclopedic overview
11 sectionsContents
- Approaches
- From alkenes using carbenoid reagents
- Simmons–Smith reaction
- Using diazo compounds
- Using diazo compounds with metal catalysis
- Using free carbenes
- From alkenes using ylides
- Intramolecular cyclisation
- Other approaches
- Biosynthesis
- References
In organic chemistry, cyclopropanation refers to any chemical process which generates cyclopropane () rings. It is an important process in modern chemistry as many useful compounds bear this motif; for example pyrethroid insecticides and a number of quinolone antibiotics (ciprofloxacin, sparfloxacin, etc.). However, the high ring strain present in cyclopropanes makes them challenging to produce and generally requires the use of highly reactive species, such as carbenes, ylids and carbanions. Many of the reactions proceed in a cheletropic manner.
thumb|250px|right|The structures of the natural insecticides pyrethrin I, R = and [[pyrethrin II, R = .]]
Excerpted from Wikipedia’s “cyclopropanation” article, available under the CC BY-SA 4.0 licence.