2205-98-3

Upstream product

• 3301-81-3 spiro<2.5>octan-4-ol 
• 72761-65-0 Spiro<2.5>dec-4-en-4-yl-trifluormethansulfonat 
• 143618-68-2 Oxo-phenyl-acetic acid spiro[2.5]oct-4-yl ester 
• 185-65-9 spiro[2.5]octane 
• 935-36-4 2,2-Bis-brommethyl-cyclohexan-1-on 
• 106-93-4 ethylene dibromide 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 78293-98-8 4-spiro<2,5>octanone oxime 
• 1059-49-0 2,2-Bis-tosyloxymethyl-cyclohexan-1-on 
• 2402-57-5 2-(2-chloroethyl)cyclohexanone 
• 25059-70-5 2-chloroethyl dimethyl sulfonium iodide 
• 108-94-1 cyclohexanone 
• 70775-39-2 dimethylsulfoxonium methylide 
• 822-87-7 2-Chlorocyclohexanone 

Downstream Products

• 4423-94-3 2-ethylcyclohexanone 
• 110129-39-0 5-(4-Methoxy-benzyl)-spiro[2.5]octan-4-one 
• 110128-53-5 (4R,5R)-5-(4-Methoxy-benzyl)-spiro[2.5]octan-4-ol 
• 110128-53-5 cis-5-(4-methoxybenzyl)-spiro<5,2>-octan-4-ol 
• 52315-48-7 2-<2-(1'-Cyclohexenylethyl)>-spiro<2.5>octan 

Relevant academic research and scientific papers

Piperidine trapping of conformationally restricted cyclopropylcarbenes

Conformationally restricted cyclopropylcarbenes were formed by photolysis (300+436 nm) of the corresponding oxadiazolines, and trapped with piperidine.

2-CHLOROETHYL DIMETHYL SULFONIUM IODIDE.

Ketones are readily spiroannelated by 2-chloroethyldimethyl sulfonium iodide 1 in the presence of t-butoxide anion in t-butanol.The procedure affords a simple one step spirocyclopropanation of ketones in good yields.

RESIST COMPOSITION, METHOD OF FORMING RESIST PATTERN, POLYMERIC COMPOUND, AND COMPOUND

A resist composition including a resin component having a structural unit derived form a compound represented by formula (a0-1) (in the formula, W represents a polymerizable group-containing group; Ra01 is a group which is bonded to Ra03 to form an aliphatic cyclic group, or bonded to Ra04 to form an aliphatic cyclic group; Ra02 represents a hydrocarbon group which may have a substituent; Ra03 is a hydrogen atom or a monovalent organic group in the case where Ra01 is not bonded thereto; Ra04 is a hydrogen atom or a monovalent organic group in the case where Ra01 is not bonded thereto; and Ra05 to Ra07 each independently represents a hydrogen atom or a monovalent organic group).

Direct Oxidation of Cyclopropanated Cyclooctanes as a Synthetic Approach to Polycyclic Cyclopropyl Ketones

A series of polycyclic hydrocarbons containing cyclopropane moieties 1,2-annelated or spiro-condensed with a cyclooctane ring were investigated under oxidative conditions. Four oxidizing systems (O3 on SiO2, a dioxirane derived from trifluoroacetone, CrO3, and RuO4, generated in situ), were tested to evaluate and compare their reactivity and usefulness. RuO4 was found to be the best of them, considering its oxidative power together with the simple operating procedure. Conditions for the specific oxidation of polycyclic hydrocarbons were found. New cyclooctane derivatives containing cyclopropyl carbonyl moieties were obtained.

Combined effects on selectivity in Fe-catalyzed methylene oxidation

Methylene C-H bonds are among the most difficult chemical bonds to selectively functionalize because of their abundance in organic structures and inertness to most chemical reagents. Their selective oxidations in biosynthetic pathways underscore the power of such reactions for streamlining the synthesis of molecules with complex oxygenation patterns. We report that an iron catalyst can achieve methylene C-H bond oxidations in diverse natural-product settings with predictable and high chemo-, site-, and even diastereoselectivities. Electronic, steric, and stereoelectronic factors, which individually promote selectivity with this catalyst, are demonstrated to be powerful control elements when operating in combination in complex molecules. This small-molecule catalyst displays site selectivities complementary to those attained through enzymatic catalysis.

N-dihydroxyalkyl-substituted 2-oxo-imidazole derivatives

The invention provides the compounds represented by the formula (I) in which, R stands for a dihydroxy-substituted C1-C6 alkyl group, and Cy stands for an optionally substituted C6-C10 bi- or tri-cyclic aliphati

Oxyfunctionalization of non-natural targets by dioxiranes. 5. Selective oxidation of hydrocarbons bearing cyclopropyl moieties

The powerful methyl(trifluoromethyl)dioxirane (lb) was employed to achieve the direct oxyfunctionalization of 2,4-didehydroadamantane (5), spiro[cyclopropane-1,2′-adamantane] (9), spiro[2.5]-octane (17), and bicyclo[6.1.0]nonane (19). The results are compared with those attained in the analogous oxidation of two alkylcyclopropanes, i.e., n-butylcyclopropane (11) and (3-methyl-butyl)-cyclopropane (14). The product distributions observed for 11 and 14 show that cyclopropyl activation of α-C-H bonds largely prevails when no tertiary C-H are present in the open chain in the tether; however, in the oxyfunctionalixation of 14 cyclopropyl activation competes only mildly with hydroxylation at the tertiary C-H. The application of dioxirane 1b to polycyclic alkanes possessing a sufficiently rigid framework (such as 5 and 9) demonstrates the relevance of relative orientation of the cyclopropane moiety with respect to the proximal C-H undergoing oxidation. At one extreme, as observed in the oxidation of rigid spiro compound 9, even bridgehead tertiary C-H's become deactivated by the proximal cyclopropyl moiety laying in the unfavorable eclipsed (perpendicular) orientation; at the other end, a cyclopropane moiety constrained in a favorable bisected orientation (as for didehydroadamantane 5) can activate an α methylene CH2 to compete effectively with dioxirane O-insertion into tertiary C-H bonds. Comparison with literature reports describing similar oxidations by dimethyldioxirane (1a) demonstrate that methyl(trifluoromethyl)dioxirane (1b) presents similar selectivity and remarkably superior reactivity.

Synthesis of gem-dinitro compounds with a three-membered cycle

A reaction was studied between nitrogen pentoxide in chloroform and oximes of cyclic ketones, derivatives of bicyclo[3.1.0]hexane, bicyclo[4.1.0]heptane, spiro[2.4]heptane, spiro[2.5]octane, resulting in the corresponding gem-dinitro compounds.

SOLVOLYTIC HYDROPEROXIDE REARRANGEMENTS V. A Stereoselective Synthesis of trans-Fused Butyrolactones.

Stereoselective rearrangement of cis-5-(4-methoxybenzyl)-spirooctan-4-ol cis-1 in acidified THF-90percent H2O2 affords 9-oxabicyclononyl hydroperoxydes 7 and 8 which are converted to medium-ring, keto-butyrolactones 2 and 3.

On the Mechanism of the Ozonolysis of C-H Bonds: Influence of SiO2-Solvent, H/D Isotope Effect, Intermediates

Ozonation of trans-1,2-dimethylcyclohexane (1) in CFCl3 solution, on dry silica gel, and in CFCl3/SiO2 suspension under otherwise equivalent conditions leads to comparable product distributions with very similar rates.In the presence of SiO2 mainly the fraction of retention product is definitely higher.Any activation of substrate or ozone is therefore highly improbable.This is supported by the kinetic H/D isotope effects for trishomobarrelene (10b) and spirooctane (12b), which both in solution and on SiO2 are found to be equal within the error limits.Upon ozonation of trishomobarrelene (10), trishomobullvalene (15), hexahydrobullvalene (7), and norcarane (20) hydrotrioxides occur as detectable intermediates which decompose above -40 deg C to give alcohols and singlet oxygen.Especially the secondary representatives from 7 and 20 are the first of their kind ever fully characterized by 1H NMR spectroscopy.