Neohexene is the
hydrocarbon compound
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ex ...
with the
chemical formula
In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...
. It is a colorless liquid, with properties similar to other
hexene
In organic chemistry, hexene is a hydrocarbon with the chemical formula . The prefix "hex" is derived from the fact that there are 6 carbon atoms in the molecule, while the "-ene" suffix denotes that there is an alkene present—two carbon atom ...
s. It is a precursor to commercial
synthetic musk
Synthetic musks are a class of synthetic aroma compounds to emulate the scent of deer musk and other animal musks (castoreum and civet). Synthetic musks have a clean, smooth and sweet scent lacking the fecal notes of animal musks. They are used as ...
perfumes.
Preparation and reactions
Neohexene is prepared by
ethenolysis
In organic chemistry, ethenolysis is a chemical process in which internal olefins are degraded using ethylene () as the reagent. The reaction is an example of cross metathesis. The utility of the reaction is driven by the low cost of ethylene ...
of diisobutene, an example of a
metathesis reaction:
:
It is a building block to synthetic musks by its reaction with
''p''-cymene. It is also used in the industrial preparation of
terbinafine
Terbinafine, sold under the brand name Lamisil among others, is an antifungal medication used to treat pityriasis versicolor, fungal nail infections, and ringworm including jock itch and athlete's foot. It is either taken by mouth or applied to ...
.
In the study of
C-H activation, neohexene is often used as a hydrogen acceptor.
[{{cite journal, last1 = Liu, first1 = Fuchen, last2 = Pak, first2 = Esther B., last3 = Singh, first3 = Bharat, last4 = Jensen, first4 = Craig M., last5 = Goldman, first5 = Alan S., title = Dehydrogenation of ''n''-Alkanes Catalyzed by Iridium "Pincer" Complexes: Regioselective Formation of α-Olefins, journal = ]J. Am. Chem. Soc.
The ''Journal of the American Chemical Society'' is a weekly peer-reviewed scientific journal that was established in 1879 by the American Chemical Society. The journal has absorbed two other publications in its history, the ''Journal of Analytic ...
, year = 1999, volume = 121, issue = 16, pages = 4086-4087, doi = 10.1021/JA983460P
References
Alkenes