Carbon−Carbon Coupling of Two Alkenyl Fragments on a Saturated Compound

1997 ◽  
Vol 16 (13) ◽  
pp. 2919-2928 ◽  
Author(s):  
Miguel A. Esteruelas ◽  
Fenghui Liu ◽  
Enrique Oñate ◽  
Eduardo Sola ◽  
Bernd Zeier
Keyword(s):  
Saturated Compound

PITHECOLOBINE, THE ALKALOID OF PITHECOLOBIUMSAMAN BENTH. I

1952 ◽  
Vol 30 (10) ◽  
pp. 761-772 ◽  
Author(s):  
K. Wiesner ◽  
D. M. MacDonald ◽  
Z. Valenta ◽  
R. Armstrong
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Ultraviolet Spectrum ◽  
Hydroxyl Group ◽  
Lithium Aluminum ◽  
Amino Groups ◽  
Saturated Compound ◽  
Secondary Amino ◽  
Trimethyl Amine ◽  
Methylene Group

Pithecolobine, C22H46N4O2, has a lactam group, one primary and two secondary amino groups, and a hydroxyl group. Lithium aluminum hydride converts it into a monocyclic saturated compound, desoxypithecolobine, C22H48N4. Hofmann degradation of this compound gives tetramethylputrescine, trimethyl amine, a doubly unsaturated base C16H31N with a terminal methylene group, and a base C16H34N2. Heating with selenium yields a hydrocarbon, C12;H24–26, with a sequence of six or more CH2 groups. A crystalline oxygen-free compound with two nitrogens (m.p.94 °C.) is also obtained, the ultraviolet spectrum of which is almost identical with aminopyridine.

scholarly journals Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks

2015 ◽  
Vol 11 ◽  
pp. 1876-1880 ◽  
Author(s):  
Meriem K Abderrezak ◽  
Kristýna Šichová ◽  
Nancy Dominguez-Boblett ◽  
Antoine Dupé ◽  
Zahia Kabouche ◽  
...  
Keyword(s):  
Methyl Acrylate ◽  
Ring Opening ◽  
Building Blocks ◽  
Epoxide Ring ◽  
Cross Metathesis ◽  
Saturated Compound ◽  
Polyfunctional Compounds ◽  
The Cross ◽  
High Yields ◽  
Nucleophilic Ring Opening

The cross metathesis of 1,2-epoxy-5-hexene (1) with methyl acrylate and acrylonitrile was investigated as an entry to the synthesis of polyfunctional compounds. The resulting cross metathesis products were hydrogenated in a tandem fashion employing the residual ruthenium from the metathesis step as the hydrogenation catalyst. Interestingly, the epoxide ring remained unreactive toward this hydrogenation method. The saturated compound resulting from the cross metathesis of 1 with methyl acrylate was transformed by means of nucleophilic ring-opening of the epoxide to furnish a diol, an alkoxy alcohol and an amino alcohol in high yields.

scholarly journals A study of catalytic actions at solid surfaces. II.—The transference of hydrogen from saturated to unsaturated organic compounds in the liquid state in presence of metallic nickel

1919 ◽  
Vol 96 (678) ◽  
pp. 322-329 ◽  
Keyword(s):  
Organic Compound ◽  
Organic Compounds ◽  
Liquid State ◽  
Intermediate Compound ◽  
Solid Surfaces ◽  
Metallic Nickel ◽  
Saturated Compound ◽  
Unstable Type ◽  
Unsaturated Organic Compound ◽  
Intermediate System

It has been shown in the first part of this series that hydrogenation in the liquid state at a surface of metallic nickel is to be considered as effected by the temporary union of the unsaturated organic compound and of hydrogen with the nickel, followed by a breakdown of this intermediate system into nickel and the saturated compound. This explanation is a development of the “intermediate compound” theory of catalysis first put forward by De la Rive and differs from the older view mainly in that it postulates an intermediate system of a very loose unstable type, similar to that produced between the natural enzymes, water (or oxygen), and the compounds attacked by the latter, during enzymic catalysis.

Nucleophilic and acid-catalyzed cleavage of the cyclopropane rings of β,γ-unsaturated α-spirocyclopropyl ketones

1983 ◽  
Vol 61 (1) ◽  
pp. 78-85 ◽  
Author(s):  
Peter Yates ◽  
Patrick Hugh Helferty ◽  
Paul Mahler
Keyword(s):  
Nucleophilic Addition ◽  
Cyclopropane Ring ◽  
Sodium Hydride ◽  
Ring Cleavage ◽  
Similar Treatment ◽  
Torsional Strain ◽  
Rate Of Reaction ◽  
Saturated Compound ◽  
Acid Catalyzed ◽  
Rapid Protonation

Treatment of isophorone (8) with sodium amide and 1,2-dibromomethane gives 6,6-dimethyl-8-methylenespiro[2.5]octan-4-one (9) and 6,6,8-trimethylspiro[2.5]oct-7-en-4-one (10); similar treatment of 3-methylcyclohex-2-en-1-one (5) gives analogous spiro compounds 6 and 7 together with 8-methylenedispiro[2.1.2.3]decan-4-one (11) and 8-methyldispiro[2.1.2.3]dec-8-en-4-one (12). The spiro ketones 6, 7, 9, and 10 undergo homoconjugate nucleophilic addition on being heated in morpholine with cleavage of the cyclopropane rings to give 2-[2-(4-morpholinyl)ethyl]cyclohex-2-en-1-ones. The rates of reaction are much greater for the exo methylene compounds 6 and 9 than for their endo isomers 7 and 10, but the rate of reaction of 10 is only slightly greater than that of the corresponding saturated compound, 6,6,8-trimethylspiro[2.5]octan-4-one (15). A corresponding rate differential between 9 and 10 is observed in their reactions with isophorone (8) and sodium hydride to give 2,2′-(ethanediyl)bis[3,5,5-trimethylcyclohex-2-en-1-one] (18). The acceleration in the cases of 6 and 9 relative to that of 15 is attributed to spiroactivation by both the carbonyl and exocyclic ethylenic groups; the much smaller effect of the endocyclic ethylenic groups in the cases of 7 and 10 is ascribed to torsional strain in the transition states for ring opening. The spiro ketones 6, 7, 9, and 10 also undergo acid-catalyzed cyclopropane ring cleavage in ethanol, giving 2-(2-ethoxyethyl)cyclohex-2-en-1-ones. Again the exo methylene compounds 6 and 9 react much more rapidly than their endo isomers 7 and 10; this is considered to be due to factors analogous to those operative in the nucleophilic addition reactions and/or the more rapid protonation of the exo methylene compounds.

The Structure of Chlorinated Rubbers

1953 ◽  
Vol 26 (2) ◽  
pp. 411-417 ◽  
Author(s):  
René Allirot ◽  
Léon Orsini
Keyword(s):  
Chemical Composition ◽  
Natural Rubber ◽  
Maximum Degree ◽  
Chemical Structure ◽  
Chain Structure ◽  
Organic Analysis ◽  
A Value ◽  
Homogeneous Product ◽  
Saturated Compound ◽  
A Chain

Abstract Natural rubber chlorinated to the maximum degree is a homogeneous product in chemical composition and likewise in chemical structure. It is a chemically saturated compound, with a chain structure having the cyclohexane group, C10HxCl7, as the base unit. Such a structure is conceivable only if x has a value of 11, which cannot be determined precisely by any of the methods of organic analysis.

Diterpene chemistry. VIII. Synthesis of perfumery compounds from Labda-8(17),14-dien-13-ol (Manool)

1978 ◽  
Vol 31 (8) ◽  
pp. 1785 ◽  
Author(s):  
PK Grant ◽  
CK Lai
Keyword(s):  
Hydrogen Peroxide ◽  
Selenium Dioxide ◽  
Saturated Compound

Hydroxymethylation of 14,15-dinorlabd-8(17)-en-13-one (3) has led to the synthesis of a new series of intramolecular acetals related to known perfumery compounds. A novel oxidation of a saturated compound with selenium dioxide/hydrogen peroxide is reported.

Cyclophanes. XII* The Synthesis of [2,2](3,3')Biphenylo(3,6)-phenanthrenophanes and Attempted Conversions into Hepta[8]circulene

1979 ◽  
Vol 32 (2) ◽  
pp. 361 ◽  
Author(s):  
DN Leach ◽  
JA Reiss
Keyword(s):  
Ring Contraction ◽  
Factors Affecting ◽  
Spectral Evidence ◽  
Saturated Compound ◽  
Contraction Procedure

[2,2](3,3')Biphenylo(3,6)phenanthrenophane-1,15-diene (6) has been synthesized by a ring-contraction procedure from the dithiacyclophane (10). The corresponding saturated compound (5) was prepared by pyrolysis of the sulfone (12). The stereochemistry of both (5) and (6) in solution has been determined to be syn from spectral evidence and neither compound shows any evidence of conformational ring-flipping or extensive mobility. Several attempts to convert the diene (6) into hepta[8]circulene are recorded. The factors affecting the photochemical ring-closures of cyclophanedienes are discussed.

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