Nalazite se na CroRIS probnoj okolini. Ovdje evidentirani podaci neće biti pohranjeni u Informacijskom sustavu znanosti RH. Ako je ovo greška, CroRIS produkcijskoj okolini moguće je pristupi putem poveznice www.croris.hr
izvor podataka: crosbi

Reduction of adamantanone : face selection induced by 4-halo- and 4, 9-dihalo- substitution (CROSBI ID 77559)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Kaselj, Mira ; le Noble, William J. Reduction of adamantanone : face selection induced by 4-halo- and 4, 9-dihalo- substitution // Journal of organic chemistry, 61 (1996), 12; 4157-4160. doi: 10.1021/jo9601066

Podaci o odgovornosti

Kaselj, Mira ; le Noble, William J.

engleski

Reduction of adamantanone : face selection induced by 4-halo- and 4, 9-dihalo- substitution

Our studies of the stereochemistry of addition and elimination as well as those of several other groups have been based largely on the reactions of 2-adamantylidenes bearing substituents in the 5- and/or 7-positions. In these probes, the two faces at C-2 are thereby rendered electronically different while steric equivalence is maintained. We find that attack of all reagents at C-2 occurs at the zu face if an electron-withdrawing substituent is located at C-5, while we interpret as an indication that transition state hyperconjugation controls the stereochemistry. Since the product or rate ratios are usually rather modest, the though arose that, perhaps, substantially more robust effects might be expected from substituents located at C-4 and C-9. In the axial positions of these secondary carbons, substituents will clearly influence face selection at C-2 sterically, but in the equatorial ones, they should not.

bicyclo[2.2.2]octane ring-system ; nucleophilic-addition ; F-19 nmr ; hyperconjugation ; stereochemistry ; oxygenation ; solvolysis

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

nije evidentirano

Podaci o izdanju

61 (12)

1996.

4157-4160

objavljeno

0022-3263

1520-6904

10.1021/jo9601066

Povezanost rada

Kemija

Poveznice
Indeksiranost