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A kinetic approach to the mechanism of cationic polyolefinic cyclization. Simple and extended π-participation
Croatica Chemica Acta, 67 (1994), 2; 171-188. urn:nbn:hr:163:546870
Borčić, Stanko; Kronja, Olga; Humski, Krešimir

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Borčić, S., Kronja, O. i Humski, K. (1994). A kinetic approach to the mechanism of cationic polyolefinic cyclization. Simple and extended π-participation. Croatica Chemica Acta, 67. (2), 171-188. Preuzeto s https://urn.nsk.hr/urn:nbn:hr:163:546870

Borčić, Stanko, et al. "A kinetic approach to the mechanism of cationic polyolefinic cyclization. Simple and extended π-participation." Croatica Chemica Acta, vol. 67, br. 2, 1994, str. 171-188. https://urn.nsk.hr/urn:nbn:hr:163:546870

Borčić, Stanko, Olga Kronja i Krešimir Humski. "A kinetic approach to the mechanism of cationic polyolefinic cyclization. Simple and extended π-participation." Croatica Chemica Acta 67, br. 2 (1994): 171-188. https://urn.nsk.hr/urn:nbn:hr:163:546870

Borčić, S., Kronja, O. i Humski, K. (1994) 'A kinetic approach to the mechanism of cationic polyolefinic cyclization. Simple and extended π-participation', Croatica Chemica Acta, 67(2), str. 171-188. Preuzeto s: https://urn.nsk.hr/urn:nbn:hr:163:546870 (Datum pristupa: 18.04.2024.)

Borčić S, Kronja O, Humski K. A kinetic approach to the mechanism of cationic polyolefinic cyclization. Simple and extended π-participation. Croatica Chemica Acta [Internet]. 1994. [pristupljeno 18.04.2024.];67(2):171-188. Dostupno na: https://urn.nsk.hr/urn:nbn:hr:163:546870

S. Borčić, O. Kronja i K. Humski, "A kinetic approach to the mechanism of cationic polyolefinic cyclization. Simple and extended π-participation", Croatica Chemica Acta, vol. 67, br. 2, str. 171-188, 1994. [Online]. Dostupno na: https://urn.nsk.hr/urn:nbn:hr:163:546870. [Citirano: 18.04.2024.]

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Podaci o radu
Naslov (engleski)A kinetic approach to the mechanism of cationic polyolefinic cyclization. Simple and extended π-participation
AutorStanko Borčić
AutorOlga Kronja
AutorKrešimir Humski
Autorova ustanovaSveučilište u Zagrebu
Farmaceutsko-biokemijski fakultet
(Zavod za organsku kemiju)
Znanstveno / umjetničko
područje, polje i grana		PRIRODNE ZNANOSTI
Kemija
Organska kemija
Sažetak (engleski)
This review deals with the mechanism of the biomimetic olefinic cationic polycyclizations considering relative rate effects, activation parameters, substituent rate effects, a, p correlation and secondary deuterium kinetic isotope effects (KIE) in solvolysis, obtained with tertiary and benzylic substrates comprising one, two or more double bonds, respectively, sited at the same positions as in the natural precursor (C-5, C-9, C-13). Kinetic behaviour of substrates with one double bond at position 5 (models for mono- cyclization) which are structurally related to structures 16U and 22U suggests that the formation of the first cyclohexane ring is a concerted process with some exceptions (16U with p-OCH3). In solvolysis of chlorides with double bonds at positions 5 and 9 (28 and 29U) extended it-parcipation occurs, i.e. both double bonds of the aliphatic chain are involved in the rate determining step. Substrastes with more then two double bonds (30U and 31U) solvolyze by way of extended 7i-participation. It remains unclear if two or three double bonds are involved. The paper also shows clear evidence that the magnitude of 3-deuterium secondary KIE are the most sensitive probe for neighboring group participation.
Jezikengleski
Vrsta publikacijeOstalo - Ostalo
Status objaveObjavljen
Vrsta recenzijeRecenziran
Verzija publikacijeObjavljena verzija rada (izdavačev PDF)
Naslov časopisaCroatica Chemica Acta
Brojčani podacivol. 67, br. 2, str. 171-188
p-ISSN0011-1643
e-ISSN1334-417X
URN:NBNurn:nbn:hr:163:546870
Datum objave publikacije1994
URL dokumentahttps://hrcak.srce.hr/136883
Vrsta resursaTekst
Prava pristupaOtvoreni pristup
Uvjeti korištenjaIkona licence Zaštićeno autorskim pravom.
Datum i vrijeme pohrane2020-04-29 15:05:21