Nucleophilic and organometallic displacement reactions of allylic compounds: stereo-and regiochemistry

Tetrahedron

Volumn 36, Issue 13, 1980, Pages 1901-1930

  Magid, Ronald M ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 49149145492     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(80)80203-1     Document Type: Article

References (260)

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2. Mechanism and kinetics of substitution at a saturated carbon atom
3. 1. Rearrangement and substitution in anionotropic systems. Part 1. Test for bimolecular isomerisation in ?-phenylallyl esters
4. 2. Rearrangement and substitution in anionotropic systems. Part II. Test for bimolecular rearrangement, and confirmation of the ionic mechanism of rearrangement, from product compositions in substitutions of ?- and ?-methylallyl halides
5. 3. Rearrangement and substitution in anionotropic systems. Part III. Mechanism of, and equilibrium in, anionotropic change
6. Application of the successive labelling technique to some carbon, nitrogen and chlorine isotope effect studies of organic reaction mechanisms
7. Demonstration of bimolecular substitution with anionotropic rearrangement (S N2?) in 1-methylallyl bromide
8. The S N2? mechanism. Chloride ion-catalysed isomerization of ?- and ?-methylallyl chloride
9. 640. The kinetics and mechanism of nucleophilic displacements in allylic systems. Part I. Reaction of 3 : 3-dichloroprop-l-ene with the ethoxide ion
10. 641. The kinetics and mechanisms of nucleophilic displacements in allylic systems. Part II. The reactions between 3 : 3-dichloroprop-l-ene and the thiophenoxide ion
11. 694. The kinetics and mechanisms of nucleophilic displacements in allylic systems. Part III. The reactions of 3 : 3 : 3-trichloro-2-methylprop-1-ene with nucleophilic reagents
12. 714. The kinetics and mechanisms of nucleophilic displacements in allylic systems. Part IV. The reaction of 1 : 1-dimethylallyl chloride with the thiophenoxide ion
13. The kinetics and mechanisms of nucleophilic displacements in allylic systems. Part VII. Solvent effects in the reactions of the dichloropropenes and related compounds
14. 519. Kinetics and mechanisms of nucleophilic displacement in allylic systems. Part IX. Bimolecular substitution with rearrangement in the reaction of 1-tert.-butylallyl chloride with ethoxide ion
15. Sigma-Pi Interaction Accompanied by Stereoselection
16. The Stereoselection Rule for Electrocyclic Interactions
17. Theory of orientation and stereoselection
18. Stereochemistry of SN2′ reactions
19. Evidence for a synfacial nucleophilic displacement with allylic rearrangement. Mechanistic conclusions. Preliminary communication
20. Introduction
21. The Stereochemistry of the SN2' Reaction. II1
22. Stereochemistry of the SN2' reaction in cyclohexenyl systems
23. Stereochemistry of the S N2? reaction in cyclohex-2-enyl esters
24. Conformational Preferences in Cyclohexanes and Cyclohexenes
25. Conformational analysis of 2-substituted methylenecyclohexanes and 3-substituted cyclohexenes and the anomeric effect
26. Stereochemistry of the S N2? reaction with acyclic allylic esters
27. 648. Researches on acetylenic compounds. Part LXII. The interaction of amines and the stereoisomers of 5-chlorohex-3-en-1-yne
28. Stereochemistry of the SN2' reaction. "Concerted" allylic displacement in an acyclic system: anti displacement with thiolate anion
29. Steric course of the chorismate synthetase reaction and the 3-deoxy-D-arabino-heptulosonate 7-phosphate (DAHP) synthetase reaction
30. Syntheses and Absolute Configuration of (E)- and (Z)-?-Bisabolenes
31. ALKYL–ALKYL COUPLING OF LITHIUM ALKYLALUMINATES AND ALKYL–ALLYL CROSS-COUPLING OF THE ALUMINATES WITH ALLYLIC HALIDES BY THE USE OF COPPER (II) ACETATE: AN APPLICATION OF THE CATALYTIC HYDROALUMINATION OF OLEFINS TO ORGANIC SYNTHESIS
32. Douglas fir tussock moth pheromone: identification of a diene analog of the principal attractant and synthesis of stereochemically defined 1,6-, 2,6-, and 3,6-heneicosadien-11-ones
33. Stereoselective synthesis of 1,4-dienes and mono-olefins by methylcopper-induced cross-coupling of dialkenylchloroboranes with organic halides
34. The Reaction of Copper(I) Methyltrialkylborates with Allylic Halides or 2-Propynylic Halides
35. Carbon-Carbon Bond Formation by Selective Coupling of Alkylthioallylcopper Reagent with Allylic Halides
36. Regiocontrolled head-to-tail coupling of alkylthioallyl carbanions with allylic halides via lithium alkylthioallyl borates
37. A new synthesis of olefins and dienes: steroids
38. Steric course of cross coupling of organocopper reagents with allylic acetates
39. Stereoselective synthesis of olefins. Reaction of dialkylcopper-lithium reagents with allylic acetates
40. Stereochemistry of the organocuprate reactions of two cis?trans isomeric allylic ethers
41. A CONVENIENT METHOD FOR THE PREPARATION OF ALLYL ETHERS—THE REACTION OF α,β-UNSATURATED ACETALS WITH GRIGNARD REAGENTS ACTIVATED BY TITANIUM TETRACHLORIDE
42. A NEW ONE-POT CROSS COUPLING REACTION OF THE GRIGNARD REAGENTS AND ALLYL ALCOHOLS VIA 2-ALLYLOXYPYRIDINIUM SALTS
43. A REGIOSELECTIVE COUPLING REACTION OF ALLYL PYRIDYL ETHERS WITH GRIGNARD REAGENTS
44. Reactions based on the onium salts of azaaromatics
45. Substitution of allylic sulphides of benzothiazole-2-thiol with organomagnesium compounds in the presence of copper(I) iodide. A regioselective synthesis of olefins
46. Displacement of activated amino groups. The reaction of organocuprates with N,N-ditrifluromethanesulfonimides.
47. Selectivity in the design of the total synthesis of natural products
48. Cis-1,6 addition of methyllithium to oxepin-benzene oxide
49. A Highly Stereoselective Preparation of 1,4- and 1,5-Alkadienes
50. The Reaction of Bicyclo [3.2.1] octenyl Halides with Metal Hydrides
51. Lithium Aluminum Hydride Reductive Rearrangement of Allylic Acetals to Vinyl Ethers: A Synthesis of 3-Deoxy Glycals
52. Ethyl 4-iodo-2,3,4-trideoxy-α-D-threo-hex-2-enopyranoside: synthesis and dehydroiodination
53. Reaction of 2-phenylallylic alcohols with lithium aluminium hydride
54. Steric factors in the hydrogenolysis of some steroidal allylic alcohols by mixed hydrides
55. A CONVENIENT METHOD FOR THE PREPARATION OF OLEFINS BY REDUCTIVE DEMETHOXYLATION OF ALLYL METHYL ETHERS USING TiCl4–LiAlH4
56. A Stereoselective Synthesis of Allylic Alcohols via the Reduction of α,β-Unsaturated Epoxides with Diborane
57. The Reaction of Primary and Secondary Alcohols with Phosphorus Trichloride/Dimethylformamide Reagents
58. Some anomalous products from the attempted halogenation of unsaturated alcohols by the complex from dimethyl sulphide and N-halogenosuccinimide
59. Conversion of Dithiocarbamates to Iodides viaS-Alkylation
60. Reviews
61. Reviews
62. Mechanism
63. Mechanism
64. Mechanism
65. Mechanism
66. Mechanism
67. SN? reactions involving organocuprate reagents
68. Total synthesis of prostaglandin-A2 through SN? reaction of an allylic epoxide and a heterocuprate reagent
69. Synthesis of 12-alkyl analogues of prostaglandin-A2
70. A new allylation reaction of the copper(I) salt of enamines with 2-allyloxybenzimidazoles.
71. Copper(I) acetylide induced substitution in allylic ethers of benzothiazole. Regio- and stereoselective synthesis of 1,4-enynes.
72. A convenient synthetic sequence for the deuterium labeling of olefins in the allylic position