Southwest Retort, Volume 13, Number 6, February 1961 Page: 9
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mechanisms of these and other free radical
rearrangements will be discussed.
New Chemistry of Free
Radicals in Solution
The recent study of the chemistry of
free radicals in solution has provided the
organic chemist with many new synthetic
tools. For example, substitutions via free-
radical, chain reactions proceed with ease
with saturated hydrocarbons and aliphatic
substances. Chlorinations with chlorine
and light or with sulfuryl chloride and
peroxides, brominations with bromine and
light, carboxylations with oxalyl chloride,
and light-induced sulfonations with sul-
furyl chloride and pyridine are of this
Carbon to carbon condensations can be
effected by reactions of acetyl peroxide
and t-butyl peroxide with various organic
substances, thermal decompositions of
neo-bis-nitriles, electrolyses of carboxylic
acids, and metal-salt catalyzed Grignard
reactions. Unique products can be pre-
pared by the light- and per'oxide-initiated
additions of polyhalomethanes, aldehydes,
2 -haloesters and other substances to ole-
fins. The additions of amines, alcohols,
ketones, and esters to olefins are the most
recent developments in this field. The
photochemical reactions of diasomethane
with polyhalomethanes give product of
various types dependent upon the particu-
lar halide used I (CCII CH.N., N-._ }
C(CH.,CL,) ; CBr, CH.N., = CH._Br.,
-- Br._C - CH_ N. _. I)iasomethane
reacts similarly with oc -haloesters
[ BrCH.,COOCFH: - - CH,N., N.,
BrCH._CH,COOCH:;; C::()C()OCI: .
CHN., - N., (CI(CH.):sO(CO)C)()H:; ].
Other reactions such as the autoxida-
tion of organic substances and the con-
trolled decompositions of hydroperoxides
are useful in synthesis. Certain free radical
reactions in the presence of 1,3-dienes
yield unusual dimars of an interesting
type. These reactions, and their theoretical
and practical importance as a new and
rapidly-developing part of organic chem-
istry, will be discussed.
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American Chemical Society. Dallas/Fort Worth Section. Southwest Retort, Volume 13, Number 6, February 1961, periodical, February 1961; [Dallas, Texas]. (digital.library.unt.edu/ark:/67531/metadc111077/m1/9/: accessed June 26, 2017), University of North Texas Libraries, Digital Library, digital.library.unt.edu; .