69432-94-6

Usage

Uses

Used in Organic Synthesis:
(2E)-2-methyl(1,1,1-~2~H3)but-2-ene serves as a valuable component in organic synthesis, where its carbon-carbon double bond can be exploited to form a variety of chemical products. The presence of deuterium in the molecule may offer specific advantages in certain reactions, such as improved stability or altered reaction kinetics.
Used as a Starting Material in Chemical Production:
This alkene can be utilized as a starting material for the production of other chemicals, taking advantage of its reactive double bond and deuterium-containing structure. The applications can span across different industries, including pharmaceuticals, materials science, and specialty chemicals, where its unique properties can be harnessed to create novel products or improve existing ones.

Upstream product

• 90466-19-6 E-1-bromo-1,1-dideuterio-2-methylbut-2-ene 
• 503-17-3 dimethylacetylene 
• 80-59-1 Tiglic acid 
• 71831-22-6 E-1,1-dideuterio-2-methylbut-2-en-1-ol 
• 6622-76-0 methyl (E)-2-methyl-2-butenoate 
• 71831-23-7 C₆H₁₀⁽²⁾H₂O₃S 

Relevant academic research and scientific papers

Control of regioselectivity by the lone substituent through steric and electronic effects in the nitrosoarene ene reaction of deuterium-labeled trisubstituted alkenes

For the ene reaction of 4-nitronitrosobenzene (ARNO) with a variety of primary and secondary lone alkyl-substituted substrates, the twix/twin regioselectivity is constant at about 85:15. In contrast, for the lone tert-butyl group and for lone aryl substituents, the twix regioisomer is obtained exclusively. These regioselectivities have been rationalized in terms of steric interactions and coordination between the enophile and the substrates in the transition states of the first reaction step.

Reactions of phenyltriazolinedione with alkenes. Stereochemistry of methanol adducts to aziridinium imide intermediates

The addition of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) and the stereochemistry of methanol/PTAD adduct formation with cis- and trans-2-butenes, 1-methylcyclopentene, (E)-2-methyl-2-butene-1,1,1-d3 and substituted indenes (indene, 2-methylindene, 2,3-dimethylindene) have been investigated. There is no loss of stereochemistry in the addition of MeOH and PTAD to butenes, 1-methylcyclopentene, 2-methyl-2-butene, and indene. However, in methyl-substituted indenes 9 and 14, loss of stereochemistry at the reaction center is observed. An aziridinium imide (AI) is proposed as an intermediate in all these systems. The stability of the AI intermediate and its equilibration with an open zwitterion depend on the particular system. Only in the benzylically-stabilized tertiary indenes is the open zwitterion stable enough to cause loss of stereochemistry.

Investigations of the magnitude of steric and α deuterium kinetic isotope effects in a carbon-carbon bond-forming reaction of a permethylscandocene complex

No measurable isotope effect is observed in the reaction of (Cp*-d15)2Sc-CH3 (1a, Cp* = η5-C5(CH3)5) with CD3CCCH3 to yield a mixture of (Cp*-d15)2Sc-C(CD3)C=C(CH3)2 (2a) and (Cp*-d15)2Sc-C(CH3)C=C(CH3)(CD3) (2b) (2b:2a = 1.01 +/- 0.02:1).Thus steric repulsions between the 2-butyne methyl group and the scandium-bound methyl group are not sufficiently severe to give rise to a measurable steric deuterium kinetic isotope effect.Similarly, 1a reacts with CH3CCCH3 at approximately the same rate as does (Cp*-d15)2Sc-CD3 (1b), producing a mixture of (Cp*-d15)2Sc-C(CH3)C=C(CH3)2 (2c) and (Cp*-d15)2Sc-C(CH3)C=C(CD3)(CH3) (2d) (k2c/k2d=1.02+/-0.07).The implication from the latter finding is that a 2-CH2-H)> α agostic interaction is likely not present in the transition state for 2-butyne insertion into the scandium methyl bond of 1.

Lewis Acid Catalysis of the Ene Addition of Chloral and Bromal to Olefins; Stereochemical and Mechanistic Studies

The Lewis acid catalysed ene additions of chloral and bromal to alkenes are completely regiospecific, moderately regioselective, and often highly stereoselective.Diastereoselectivity in the addition to (-)-β-pinene was a function of the Lewis acid, and with TiCl4 essentially quantitative asymmetric induction was observed.The stereochemical phenomena are explained satisfactory by assuming the active enophiles possess transoid structures such as (1), that a concerted or rapid stepwise mechanism operates, and that product formation occurs predominantly through the least hindered encounter complex of the olefin and (1).In the case of 2-methylbut-2-ene, however, there is some evidence for an additional stereoelectronic contribution, the 'cis-effect'.Stereochemical assignements are supported by X-ray structural data.Ketones, hydrohalogenated ene adducts, or rearrangement products are formed (mainly in the addition to olefins of moderate reactivity) indicating the participation of Friedel-Crafts type dipolar intermediates.The ene adducts themselves could be formed via dipolar intermediates or in competing 'concerted' reactions; the stepwise mechanism must operate in some reactions because of the observation of Wagner-Meerwein rearrangements.Olefin reactivity over the series, measured by the competitive technique, towards chloral-AlCl3 showed a ca. 900-fold variation in rate; 'ene' reactivity decreases more steeply.