Metal-Catalyzed Addition to Olefins

doi:10.1016/b978-0-12-418250-9.50011-5

Organometallic Mechanisms and Catalysis 1978

DOI: 10.1016/b978-0-12-418250-9.50011-5

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Metal-Catalyzed Addition to Olefins

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1997

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Cited by 3 publications

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Lösungsmittelfreie, durch Elektronenübertragung von Kupfer initiierte radikalische Additionen von aktivierten Halogenalkanen an Alkene

Metzger

Mahler

1995

Angewandte Chemie

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Sequenzen; Numerierung der Atome siehe Schema 1). Die aus den Elementaranalysen erhaltenen Werte (C, H und I) der Verbindungen 2, 3, 6. 8 und 10 weichen maximal um 0.3 % von den berechneten Werten ab. 2 (3,7-Dimethyltricycl0[3.3.0.0~~ ']octan-1,5-dicarbons~ure): Schmp. 166-168 "C; IR (KBr): i. = 3500-2500 (OH), 1700 (CO) em-'; 'H-NMR (200 MHz): 6 = 1.19 (s. CH,), 1.72 (d, J = 7 . 7 Hz), und 1.95 (d. J=7.7 Hz) (CH,), 8.5-9.5 [breit, [C, Cl(5)l. 179.8 (C, COOH). 3 (1,5-Diiod-3,7-dimethyltricyclo[3.3.O.03~7]octan): Schmp. 95-97 ' C (sublimiert bei 70°C/0.5 Torr); MS (70 eV): m/r(%): 388 (3) [MI", 261 (33) [M ~ I]+, 135 (200 MHz): 6 =1.19 (s, CH,), 1.94 (d, J =7.5 Hz) und 2.19 (d, J =7.5 Hz) (CH,); 6 (4,5-D~methyl-l,8-diphenyl-l5-oxahexacyclo[6.6.1.12~~.14~7.02~',09~14]heptddeca-9.11.13-trien:Schmp. 188-189'C;MS(70eV):m/z(%):404(8)[M]"+

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Lösungsmittelfreie, durch Elektronenübertragung von Kupfer initiierte radikalische Additionen von aktivierten Halogenalkanen an Alkene

Metzger

Mahler

1995

Angewandte Chemie

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Radical Additions of Activated Haloalkanes to Alkenes Initiated by Electron Transfer from Copper in Solvent‐Free Systems

Metzger

Mahler

1995

Angew. Chem. Int. Ed. Engl.

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with 1-Ni, the trimer 6-Ni, is obtained. Thus not only does this building block approach give access to arrays of different sizes but also systematic and controlled metalation is easily achieved.Porphyrin 1 is an ideal building block for the synthesis porphyrin arrays. It is easily prepared on a large scale and in high yield, and can be metalated as required. The array-forming reactions (to form dimeric and trimeric porphyrins) are higher yielding than for comparable molecules prepared by linear synthetic strategies. Overall we believe that this building block approach has great promise, and our current research is directed towards using 1 and similar building blocks to construct larger arrays. Experimental Procedure1 : Phosphoniiim salt 2 (1 13 mg. 0.12 mmol) and dialdehyde 3 (18 mg, 0.13 mmol) were dissolved in CH,CI, (20 mL) and stirred at room temperature before 1 &diazabicyclo[5.4.0]undec-7-ene (DBU) (0.5 mL) was added. After 1 min. the reaction mixture was chromatographed (silica gel. 1 : 1 CH,CI,: hexane) to give a purple solid. The solid, a cisitrans mixture of products, was dissolved in CH,CI, (40 mL).

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Radical Additions of Alkyl 2‐Haloalkanoates and 2‐Haloalkanenitriles to Alkenes Initiated by Electron Transfer from Copper in Solvent‐Free Systems

Metzger¹,

Mahler²,

Francke³

1997

Liebigs Ann./Recl.

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Alkyl 2‐iodoalkanoates 2, and 2‐iodoalkanenitriles 15 were added, with copper powder, to the 1‐alkenes 1a, e, f, and h, and to the alkenes 1b, c, d, and g with a 1,2‐dialkyl substituted double bond, to give, respectively, γ‐lactones and 4‐iodoalkanenitriles in very good yields. No solvent was used. The reaction is a free radical addition initiated by electron transfer from copper to the activated iodoalkane. Yields were lower using the respective bromo compounds. In situ formation of the iodo compounds, by addition of stoichiometric amounts of sodium iodide to the reaction mixture, gave improved yields. In the case of the methyl bromomalonates 6, the addition of sodium iodide proved to be unnecessary. The diastereoselectivity of the addition reaction by relative 1,3‐asymmetric induction was rationalized by consideration of the steric interactions of the substituents in the transition state which is formed in the process of iodine transfer to the chiral adduct radical.

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Metal-Catalyzed Addition to Olefins

Cited by 3 publications

References 76 publications

Lösungsmittelfreie, durch Elektronenübertragung von Kupfer initiierte radikalische Additionen von aktivierten Halogenalkanen an Alkene

Lösungsmittelfreie, durch Elektronenübertragung von Kupfer initiierte radikalische Additionen von aktivierten Halogenalkanen an Alkene

Radical Additions of Activated Haloalkanes to Alkenes Initiated by Electron Transfer from Copper in Solvent‐Free Systems

Radical Additions of Alkyl 2‐Haloalkanoates and 2‐Haloalkanenitriles to Alkenes Initiated by Electron Transfer from Copper in Solvent‐Free Systems

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