3419-66-7

Usage

Uses

1. Used in Catalyst Research:
1-TERT-BUTYL-1-CYCLOHEXENE is used as a substrate to investigate the catalytic activity and BET (Brunauer-Emmett-Teller) surface area of different desilicated TS-1 zeolite samples. This application is significant in the field of catalysis, as it helps researchers understand the efficiency and effectiveness of various zeolite catalysts in chemical reactions.
2. Used in Chemical Synthesis:
1-TERT-BUTYL-1-CYCLOHEXENE can be utilized as an intermediate in the synthesis of various chemicals and pharmaceuticals. Its unique structure allows for further functionalization and modification, making it a valuable building block in the development of new compounds with specific properties and applications.
3. Used in Material Science:
1-TERT-BUTYL-1-CYCLOHEXENE may also find applications in material science, particularly in the development of new polymers and materials with tailored properties. Its cyclohexene ring and tert-butyl group can contribute to the overall structure and characteristics of the resulting materials, potentially leading to innovative applications in various industries.
4. Used in Analytical Chemistry:
1-TERT-BUTYL-1-CYCLOHEXENE can be employed as a reference compound or standard in analytical chemistry, particularly in techniques such as gas chromatography and mass spectrometry. Its distinct chemical properties make it suitable for calibrating instruments and validating analytical methods.

Synthesis Reference(s)

The Journal of Organic Chemistry, 36, p. 3826, 1971 DOI: 10.1021/jo00823a611Synthesis, p. 147, 1971 DOI: 10.1055/s-1971-21684

InChI:InChI=1/C10H18/c1-10(2,3)9-7-5-4-6-8-9/h7H,4-6,8H2,1-3H3

Upstream product

• 253185-03-4 tert-butylbenzene 
• 507-20-0 tertiary butyl chloride 
• 110-83-8 cyclohexene 
• 13491-79-7 2-tert-butylcyclohexan-1-ol 
• 75-89-8 2,2,2-trifluoroethanol 
• 7453-05-6 toluene-4-sulfonic acid-(trans-4-tert-butyl-cyclohexyl ester) 
• 7453-04-5 cis-4-tert-butylcyclohexyl tosylate 
• 98-52-2 4-(1,1-dimethylethyl)-cyclohexanol 
• 20344-52-9 1-tert-butylcyclohexanol 
• 594-19-4 tert.-butyl lithium 
• 108-94-1 cyclohexanone 
• 88802-80-6 1,2,2-trimethylcycloheptanol 
• 79239-09-1 2-(1-trimethylsilylmethylcyclohexyl)propan-2-ol 
• 286-20-4 cyclohexene oxide 

Downstream Products

• 7583-74-6 1,2-epoxy-1-t-butylcyclohexane 
• 69035-58-1 1-(tert-butyl)cyclohex-2-en-1-ol 
• 77931-76-1 2-tert-butylcyclohex-2-en-1-ol 
• 97741-62-3 1-tert-butylcyclohexane-cis-1,2-diol 
• 147544-32-9 2-tert-Butyl-cyclohex-2-enyl-hydroperoxide 
• 99942-89-9 Acetic acid 3-tert-butyl-cyclohex-2-enyl ester 
• 3178-22-1 tert-butylcyclohexane 
• 17299-35-3 3-(tert-butyl)cyclohex-2-en-1-one 
• 97741-69-0 (3aR,7aR)-3a-tert-Butyl-2-phenyl-hexahydro-benzo[1,3]dioxole 
• 5448-22-6 trans-2-tert-butylcyclohexan-1-ol 
• 98104-30-4 trans 2-tert-butylcyclohexanol 

Relevant academic research and scientific papers

Enantioselective Hydroazidation of Trisubstituted Non-Activated Alkenes

A one-pot procedure for the enantioselective hydroazidation of non-activated trisubstituted alkenes is described. Hydroboration with monoisopinocampheylborane (IpcBH2) provides dialkylboranes that are in situ selectively converted into monoalkyl-substituted catecholboranes; these undergo radical azidation upon treatment with benzenesulfonyl azide and a radical initiator. Enantiomerically enriched azides were thus obtained in yields of 59–81 % and enantioselectivities of up to 94:6 e.r. (98:2 e.r. if the intermediate dialkylborane is purified by crystallization). A rapid access to enantiomerically pure (+)-rodocaine is also described. The use of other arenesulfonyl radical traps enables enantioselective hydroallylation, hydrosulfanylation, and hydrobromination reactions with yields of 71–86 %.

Me2s-induced highly selective reduction of aldehydes in the presence of ketones involving aldehyde-selective rate enhancement: A triruthenium cluster-catalyzed hydrosilylation

Addition of appropriate amounts of Me2S unusually accelerated the hydrosilylation of aldehydes catalyzed by [Ru3(CO)7(Acy)] (1, Acy: μ3-η2,η3,η5-acenaphthylene). The reduction of

An efficient method for chlorination of alcohols using PPh3/Cl3CCONH2

A new and convenient method for the chlorination of alcohols utilizing PPh3/Cl3CCONH2 is addressed. Various alcohols could smoothly be converted into their corresponding alkyl chlorides in high yield under mild conditions with short reaction times. A mechanism is disclosed with the evidence of inversion of configuration of the analogous alkyl chloride derived from R-(-)-2-octanol.

Catalytic asymmetric epoxidation

A compound and method for producing an enantiomerically enriched epoxide from an olefin using a chiral ketone and an oxidizing agent is disclosed.

Stereospecific Substituted Alkene Synthesis by Organo Lithium Reductive Alkylation of Epoxides

Stereospecifically alkylated olefins were synthesized in good yields by reaction of various epoxides with organolithium reagents with concommitant introduction of the alkyl group.

Composition of Mixtures of Hydrocarbons after BIRCH-Reduction of Substituted Benzenes and Acid Catalyzed Addition of Alcohols to Alkylsubstituted Cyclohexenes and Carbohexa-1,4-dienes

10 different benzene hydrocarbons 1, indane, tetraline, anisol and phenol are reduced by sodium in liquid ammonia in the presence of methanol to the BIRCH products 2.The product mixture compositions are determined through capillary GLC.On storage at +6 deg C some rearomatization of the 1,4-cyclohexadienes 2 occurs.Data of the 1H- and 13C-.n.m.r. spectra and also mass spectra of the BIRCH 1,4-dienes 2 are given.For comparison 4-alkoxycyclohexenes 4 and 1-alkoxy-1-methylcyclohexanes 8 are prepared and spectroscopically characterized.Acid-catalyzed addition of alcohols to the 1,4-cyclohexadienes systems is a slow process and gives the 4-alkoxy-4-alkylcyclohex-1-enes (4) only in moderate yields up to 30percent.Most of the products are dimers 5 and also oligomers 6 of the parent hydrocarbons 2.

Olefins from Crowded Carbonyl Compounds with tert-Butyllithium (tert-Butylmagnesium Chloride)/Thionyl Chloride. Study of Carbocationic Reaction Intermediates and Rearrangement-Cleavage under Stable Ion Conditions Using 13C NMR Spectroscopy

Crowded carbonyl compounds when reacted with tert-butyllithium or tert-butylmagnesium chloride followed by thionyl chloride treatment give in an one-pot reaction olefins in good to excellent yields.In the case of highly crowded tertiary systems the reaction occurs either by rearrangement followed by the loss of a tert-butyl group (as isobutylene) or rearrangement accompanied by deprotonation, indicating the carbocationic nature of the process.The nature of the intermediate carbocation and their cleavage-rearrangement process was probed in SbF5/SO2ClF solution of thecorresponding alcohols under stable ion conditions using 13C NMR spectroscopy.

Carbonium Ion Rearrangements Controlled by the Presence of a Silyl Group

γ-Silyl tertiary alcohols rearrange in protic acid with 1,2-shift of hydride, phenyl, or alkyl groups, and loss of the silyl group to give alkenes.The placing of the silyl group thus controls the carbonium ion rearrangement in a preparatively useful way.Methoxycarbonyl groups do not migrate; instead, cyclopropanes are formed, except when the conformation suitable for cyclopropane formation is unattainable.When the alkene product is 2,2-disubstituted, it can be reprotonated under the reaction conditions and does not therefore always survive.This can be avoided by carrying out the reaction using a Lewis acid on the silyl ether.The starting γ-silyl alcohols are prepared by a variety of versatile methods.

Solvolysis Reactions and Force Field Calculations with Epimeric Cyclohexane Derivatives

Reactions of the epimeric 4-tert-butylcyclohexyl tosylates in hexafluoroisopropyl alcohol (HFIP) (1e, 1a) allow for the first time to observe SN1-type non-stereospecific substitution, whereas conventional solvents including even trifluoroethanol yield SN2-type inversion by solvent assisted pathway (*ks).Large differences are found between the epimers in the solvent participation, measured kinetically by the Schleyer-Bentley equation.This, as well as the even enhanced elimination with the equatorial isomer 1e as compared to 1a (98percent vs. 96percent in HFIP) points to the occurence of non-chair intermediates from 1e-derivatives, and to more E2- than E1-type reactions.Kinetic measurements, including those of cis-3,5-dimethylcyclohexane esters (2a, 2e) and 3α/3β-(tosyloxy)androstanes (3a, 3e) show little differences between the equatorial esters in agreement with MM2 calculations, which establish small strain energy variations between the differently substituted twist-boat intermediates.Large differences, however, of up to 500percent are measured between the axial esters (1a, 2a, 3a), although the alkyl substituents are remote from the leaving group and do not alter the chair geometry.These variations, which demonstrate the severe limitations of the Winstein-Holness equation for solvolysis reactions, are explained by MM2 calculated significant strain differences between the educts and the corresponding substituted cyclohexenes.

ANHYDROUS FERRIC CHLORIDE DISPERSED ON SILICA GEL INDUCED RING ENLARGEMENT OF TERTIARY CYCLOALKANOLS II: A CONVENIENT HOMOLOGATION OF CYCLOALKANONES, PREPARATION OF SPIRO SYSTEMS AND PROPELLA-γ-LACTONES

The reagent obtained by mixing anhydrous FeCl3 and silica gel induced, in the lack of any solvent, dehydration of tertiary cycloalkanols, specific C4-->C5 and C5-->C6 ring enlargement, formation of spiro compounds and propella-γ-lactones and cleavage of tetrahydropyranyl ethers.