1 -Methyl-2- cyclohex

A portion of the product was heated to reflux with methanolic sodium methoxide to convert it into the thermodynamic mixture of trans- (ca. 65%) and cis- (ca. 35%) isomers. Small amounts of the isomers were collected by preparative gas chromatography using an 8 mm. by 1.7 m. column containing 15% Carbowax 20M on Chromosorb W, and each isomer exhibited the expected spectral and analytical properties. The same thermodynamic mixture of isomers was prepared independently by lithium-ammonia reduction5 of 2-allyl-3-methyl-cyclohex-2-enone [2-Cyclohexen-l-one, 3-methyl-2-(2-propcnyl)-],6 followed by equilibration with methanolic sodium methoxide. 

Analogous reactions of 3-diazobicyclo[2.2.1]heptan-2-one with perchloric acid in alcohols, such as ethanol, gave the corresponding ethers, e rfo-3-ethoxybicyclo[2.2.1]heptan-2-one (34%),, n -2-ethoxybicyclo[3.1,1]hcptan-6-onc (41%) and methyl cyclohex-3-enecarboxylate.69 Further examples of the formation of cyclobutanes from cyclopentanes via Wagner-Meerwein-type rearrangements are given in Table 2. 

Keywords (V-methyl cyclohex-1-enylanilide, inclusion crystal, [2+2]poto-cycloaddition, 3,4-dihydroquinolin-2( 177)-one... 

A second example is the spruce beetle, Dendroctonus rufipennis (Kirby) (Coleoptera Scolytidae), a major cause of mortality in mature spruce stands. Gries et al. (1992) found that the terpene verbenene (31 in Figure 19.5), was emitted from the beetles, predominantly from females, and concluded that it is a pheromone component. The oxygenated compounds seudenol, frontalin, and l-methyl-cyclohex-2-en-l-ol, were previously identified as pheromone components in this species. Attraction to verbenene alone was demonstrated in field traps, and it enhanced captures to the other pheromone components. The absolute configuration of verbenene has not been investigated. 

In the preparative application of [2 + 2]-photocycloadditions of cyclic enones to (substituted) alkenes, two factors concerning product formation are of decisive relevance, namely the regioselectivity and the (overall) rate of conversion. Regarding the regioselectivity in the addition to mono- and 1,1-disubstituted alkenes, Corey had shown that the preferred addition mode of cyclohex-2-enone to isobutene or 1,1-dimethoxyethylene was the one leading to—both cis- and trans-fused—bicyclo[4.2.0]octan-2-ones with the substituents on C(7) [8]. In contrast, in the reaction with acrylonitrile, the alternate orientation was observed to occur preferentially. Similar results were also reported by Cantrell for the photocycloaddition of 3-methyl-cyclohex-2-enone to differently substituted alkenes [14]. No significant differences in the overall rates of product formation for the different alkenes were observed in these studies. In order to explain these observed... 

The irradiation apparatus, consisting of a triple walled Dewar constructed of Pyrex, is charged with a solution of 25.0 g (0.277 mol) of 3-methyl-cyclohex-2-enone (5) in reagent-grade CH2C12. A gas outlet tube to an... 

What are the main products of metal-catalyzed autoxidation of methyl cyclohex-2-ene Why is cyclohexene more susceptible to autoxidation than cyclohexane ... 

Ans. Methyl cyclohex-2-en l-one and methyl cyclohex-2-en l-ol. Allylic stabilization of R. ... 

Figure 1.44. The different stereoisomers obtained by [2 + 2] photocycloaddition of 3-methyl-cyclohex-2-enone to Cgo (left, the newly formed stereogenic centers are marked by an asterisk), and illustration of a sector mle devised for the correlation of the absolute configuration of a 6-6 closed 1,2-adduct of Cgo to the CD band around 430 nm (right). According to the sign ((+) or (-)) of the sector in which an addend moiety (R1, R2,R3, or R4) is located, it is postulated to add a positive or negative contribution to the Cotton effect associated with the ca. 430 nm UV/Vis absorption of the fullerene chromophore.

Ozonolysis of 4,4-diphenyl-l-methyl-cyclohex-2-ene-l-ol in DCM at — 78 °C in the presence of AczO led to the oxygen-bridged 1,2-dioxocin 213 in 30% yield. Its formation is explained in terms of intramolecular trapping of the carbonyl oxide intermediate, followed by cyclic acetal formation. Since 294 is unstable and spontaneously decomposed to ketoaldehyde 215 (see Section 14.04.5.4), it was necessary to acetylate it in order to have the stable 1,2-dioxocin 213 (Scheme 60) <1995JA9927>. 

METHYL-CYCLOHEX.ANON (GERALAN, DUTCH) see XERSOO... 

Guingant and Barreto [53] published the pioneering paper describing the synthesis of ochromycinone (35) by a Diels-Alder reaction. The dienone (46) was prepared from 3-ethoxy-5-methyl-cyclohex-2-enone (45) in two steps (alternatively, a diene with SPh instead of OMe could be used). The Diels-Alder reaction with juglone (47) was catalyzed with boron triacetate to overcome the somewhat poor reactivity of the electron-deficient diene 46. The primary adduct 48 could not be isolated but directly eliminated and oxidized to ochromycinone (35) (Scheme 13). 

C10H16O2 3-hydroxycamphor 10373-81-6 21.90 0.9936 2 20740 C10H18O 2- 4-methyl-cyclohex-3-enyl)-propan-2-ol 2438-12-2 22.73 0.9060 2... 

Cyclohexanes from Alkylidenemalonates by an Intramolecular Ene Reaction Dimethyl (1 R,2 R,5 R)-2-(2 -lsopropenyl-5 -methyl-cyclohex-1 -yl)-propane-1,3-dioate[4a]. 

Formic acid methyl ester. See Methyl formate Formic acid 1-methyl-1-(4-methyl-cyclohex-3-enyl) ethyl ester. See Terpinyl formate Formic acid, neryl ester. See Neryl formate Formic acid octyl ester. See Octyl formate Formic acid, oxydi-, diethyl ester. See Diethyl pyrocarbonate... 

Draw the structure of l-methyl(cyclohex-2-ene)-l-carboxylic acid. 

To a solution of (Z)-2-((S)-6-((5)-2,2-dimethyl-l,3-dioxolan-4-yl)-4-methyl-cyclohex-3-enylidene)ethanol (701 mg, 2.94 mmol) in dry dichloromethane (20 mL) was added DBU (0.53 mL, 3.52 mmol), and the solution was cooled to 0°C. To this solution was added CCI3CN (0.44 mL, 4.41 mmol) over 15 min. The resulting reaction mixture was stirred at 0 °C for 1 h and then quenched with sat. NH4CI solution. The organic layer was washed with sat. NH4CI and then passed through a column packed with anhydrous sodium sulphate and silica gel (to remove polymeric products). The filtrate was evaporated in vacuo, and the crude imidate 36a was used directly for the next step. 

Scheme 9.113. A representation of the reduction of the cyclohexene derivative (cis-l-methyl-3-oxa-2,4-dioxobicyclo[4.3.0]-7-nonene, cis-l-methyl-cyclohex-4-ene-l,3-dicarboxyUc acid anhydride) with lithium aluminum hydride (LiAlH,) to produce the corresponding lactone, cM-l-methyl-3-oxa-4-oxobicyclo[4.3.0]-7-nonene (cw-l-methyl-l-hydroxymethylcyclohex-4-...

Methoxyethoxy)methoxy)-3-((methoxymethoxy)methyl)cyclohex-2-enon ... 

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