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In acetylene, the H–C≡C bond angles are 180°. By virtue of this bond angle, alkynes are rod-like. Correspondingly, cyclic alkynes are rare. Benzyne cannot be isolated. . The C≡C bond distance of 118 picometers (for C 2 H 2) is much shorter than the C=C distance in alkenes (132 pm, for C 2 H 4) or the C–C bond in alkanes (153 p
Alkenes react with percarboxylic acids and even hydrogen peroxide to yield epoxides: RCH=CH 2 + RCO 3 H → RCHOCH 2 + RCO 2 H. For ethylene, the epoxidation is conducted on a very large scale industrially using oxygen in the presence of silver-based catalysts: C 2 H 4 + 1/ 2 O 2 → C 2 H 4 O. Alkenes react with ozone, leading to the scission ...
Main group elements can also form π-complexes with alkenes and alkynes. The β-diketiminato aluminum(I) complex Al{HC(CMeNAr) 2 } (Ar = 2,6-diisopropylphenyl), which bears an Al-based sp x lone pair, reacts with alkenes and alkynes to give alumina (III) cyclopropanes and alumina (III) cyclopropenes in a process analogous to the formation of π ...
The B-B bond adds across alkenes and alkynes to give the 1,2-diborylated alkanes and alkenes. Using various organorhodium or organoiridium catalysts, it can also be installed onto saturated hydrocarbons: [3] CH 3 (CH 2) 6 CH 3 + [pinB] 2 → pinBH + CH 3 (CH 2) 7 Bpin. These reactions proceed via boryl complexes. Bis(pinacolato)diboron can also ...
In the case of metal-alkenes and alkynes, the strengthening of the M–C 2 R 4 and M–C 2 R 2 bond is reflected in bending of the C–C–R angles which assume greater sp 3 and sp 2 character, respectively. [8] [9] Thus strong π backbonding causes a metal-alkene complex to assume the character of a metallacyclopropane. [10]
Hydrosilylation of alkenes represents a commercially important method for preparing organosilicon compounds. The process is mechanistically similar to the hydrogenation of alkenes. In fact, similar catalysts are sometimes employed for the two catalytic processes.
Cycloalkynes have a general formula C n H 2n−4. Because of the linear nature of the C−C≡C−C alkyne unit, cycloalkynes can be highly strained and can only exist when the number of carbon atoms in the ring is great enough to provide the flexibility necessary to accommodate this geometry .
It reacts only slowly with simple terminal alkenes. It adds to alkynes to give alkenylboranes. [11] Among hindered dialkylboranes is disiamylborane, abbreviated Sia 2 BH. It also is a dimer. Owing to its steric bulk, it selectively hydroborates less hindered, usually terminal alkenes in the presence of more substituted alkenes. [12]
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