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Titolo:
PERFORMIC ACID OXIDATION OF EXO-2-SYN-7-BICYCLO[2.2.1]HEPT-5-ENEDIOL - H-1 AND C-13 NMR SPECTROSCOPIC STRUCTURE ELUCIDATION OF THE REACTION-PRODUCTS
Autore:
LAIHIA K; KOLEHMAINEN E; MANTTARI P; RYYNANEN R; MESSALARANNANPIHA M; VEPSALAINEN J; SUNDELIN JP;
Indirizzi:
UNIV JYVASKYLA,DEPT CHEM,POB 35 SF-40351 JYVASKYLA FINLAND UNIV KUOPIO,DEPT CHEM FIN-70211 KUOPIO FINLAND
Titolo Testata:
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
fascicolo: 5, volume: 52, anno: 1996,
pagine: 495 - 504
SICI:
1386-1425(1996)52:5<495:PAOOE->2.0.ZU;2-4
Fonte:
ISI
Lingua:
ENG
Soggetto:
NORBORNENE DERIVATIVES; CHEMICAL-SHIFTS; SPECTRA; MONOTERPENES; ASSIGNMENT;
Keywords:
(N)J(HH) AND (N)J(CH) COUPLING CONSTANTS; EXO-3-EXO-5-SYN-7-NORTRICYCLENETRIOL; H-1 AND C-13 NMR CHEMICAL SHIFTS; NORBORNANETETROLS; PERFORMIC ACID OXIDATION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
25
Recensione:
Indirizzi per estratti:
Citazione:
K. Laihia et al., "PERFORMIC ACID OXIDATION OF EXO-2-SYN-7-BICYCLO[2.2.1]HEPT-5-ENEDIOL - H-1 AND C-13 NMR SPECTROSCOPIC STRUCTURE ELUCIDATION OF THE REACTION-PRODUCTS", SPECT ACT A, 52(5), 1996, pp. 495-504

Abstract

Performic acid oxidation of exo-2-syn-7-bicyclo[2.2.1]hept-5-enediol (norborn-5-enediol) gives lo[2.2.1.0(2,6)]heptanetriol-(nortricyclenetriol), exo-2-endo-3-endo-5-syn-7-, exo-2-endo-3-endo5-anti-7- and 2-endo-3-exo-5-anti-7-bicyclo[2.2.1]heptanetetrols (norbornanetetrols) as reaction products, the relative amounts being 13.7%, 48.1%, 20.2% and 10.4% respectively. The structures of these polyols were elucidated using H-1 and C-13 NMR spectroscopy including 2D H-1-H-1 NOESY, H-1-H-1 COSY, C-13-H-1 COSY and C-13-C-13 INADEQUATE spectra. The reaction mechanism, which consists first of the formation of a norbornyl cation gives, after deprotonation, a triol as an end product. The mechanism leading to the three tetrols includes (1) a Wagner-Meerwein (W-M) rearrangement, (2) a 6,2-hydride shift, (3) another W-M rearrangement and (4)exo attack of the formate anion. The mechanism has been described using the known classical carbocation intermediates. The absence of threetheoretically possible reaction products can be explained by intermediates, where the attack of the formate anion on a carbocation is hindered by the vicinal exo hydroxyl group.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 01/12/20 alle ore 07:43:00