The lead tetraacetate reaction of alcohols containing a small ring. Part II. Cyclobutane‐methanols and cyclopropane‐ethanols
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1976
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Prikaz svih podataka o dokumentuApstrakt
The leadtetraacetate and lead tetraacetate/metal chloride oxidations of cyclobutane‐methanol, cyclopropane‐ethanol and the corresponding α, α‐diniethyl alcohols have been investigated and compared with the oxidative reactions of cyclobutane‐carboxylic acid, cyclopropane‐acetic acid and 4‐pentenoic acid, performed with the same reagents and under similar conditions. It was found that alcohol β‐fragmentation and acid decarboxylation follow a remarkably similar mechanistic course, affording comparable results when the substrates are of the same structural type (1, 2 and 5; 3, 4 and 6) or are converted to the same intermediate alkyl radical fragments (3, 4, 6 and 7). In addition, cyclization products formed from cyclopropane‐ethanol (dihydropyran derivative 31) and 4‐penteuoic acid (γ‐lactones 38) have been isolated and identified.
Ključne reči:
lead tetraacetate reaction of alcohols / cyclobutane‐methanols / cyclopropane‐ethanols / leadtetraacetate / α, α‐diniethyl alcoholsIzvor:
Helvetica Chimica Acta, 1976, 59, 2, 475-486Izdavač:
- Wiley
Institucija/grupa
IHTMTY - JOUR AU - Mihailović, Milhailo Lj. AU - Bošnjak, Jovan AU - Čeković, Živorad PY - 1976 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4711 AB - The leadtetraacetate and lead tetraacetate/metal chloride oxidations of cyclobutane‐methanol, cyclopropane‐ethanol and the corresponding α, α‐diniethyl alcohols have been investigated and compared with the oxidative reactions of cyclobutane‐carboxylic acid, cyclopropane‐acetic acid and 4‐pentenoic acid, performed with the same reagents and under similar conditions. It was found that alcohol β‐fragmentation and acid decarboxylation follow a remarkably similar mechanistic course, affording comparable results when the substrates are of the same structural type (1, 2 and 5; 3, 4 and 6) or are converted to the same intermediate alkyl radical fragments (3, 4, 6 and 7). In addition, cyclization products formed from cyclopropane‐ethanol (dihydropyran derivative 31) and 4‐penteuoic acid (γ‐lactones 38) have been isolated and identified. PB - Wiley T2 - Helvetica Chimica Acta T1 - The lead tetraacetate reaction of alcohols containing a small ring. Part II. Cyclobutane‐methanols and cyclopropane‐ethanols VL - 59 IS - 2 SP - 475 EP - 486 DO - 10.1002/hlca.19760590214 ER -
@article{ author = "Mihailović, Milhailo Lj. and Bošnjak, Jovan and Čeković, Živorad", year = "1976", abstract = "The leadtetraacetate and lead tetraacetate/metal chloride oxidations of cyclobutane‐methanol, cyclopropane‐ethanol and the corresponding α, α‐diniethyl alcohols have been investigated and compared with the oxidative reactions of cyclobutane‐carboxylic acid, cyclopropane‐acetic acid and 4‐pentenoic acid, performed with the same reagents and under similar conditions. It was found that alcohol β‐fragmentation and acid decarboxylation follow a remarkably similar mechanistic course, affording comparable results when the substrates are of the same structural type (1, 2 and 5; 3, 4 and 6) or are converted to the same intermediate alkyl radical fragments (3, 4, 6 and 7). In addition, cyclization products formed from cyclopropane‐ethanol (dihydropyran derivative 31) and 4‐penteuoic acid (γ‐lactones 38) have been isolated and identified.", publisher = "Wiley", journal = "Helvetica Chimica Acta", title = "The lead tetraacetate reaction of alcohols containing a small ring. Part II. Cyclobutane‐methanols and cyclopropane‐ethanols", volume = "59", number = "2", pages = "475-486", doi = "10.1002/hlca.19760590214" }
Mihailović, M. Lj., Bošnjak, J.,& Čeković, Ž.. (1976). The lead tetraacetate reaction of alcohols containing a small ring. Part II. Cyclobutane‐methanols and cyclopropane‐ethanols. in Helvetica Chimica Acta Wiley., 59(2), 475-486. https://doi.org/10.1002/hlca.19760590214
Mihailović ML, Bošnjak J, Čeković Ž. The lead tetraacetate reaction of alcohols containing a small ring. Part II. Cyclobutane‐methanols and cyclopropane‐ethanols. in Helvetica Chimica Acta. 1976;59(2):475-486. doi:10.1002/hlca.19760590214 .
Mihailović, Milhailo Lj., Bošnjak, Jovan, Čeković, Živorad, "The lead tetraacetate reaction of alcohols containing a small ring. Part II. Cyclobutane‐methanols and cyclopropane‐ethanols" in Helvetica Chimica Acta, 59, no. 2 (1976):475-486, https://doi.org/10.1002/hlca.19760590214 . .