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.
Keywords:
lead tetraacetate reaction of alcohols / cyclobutane‐methanols / cyclopropane‐ethanols / leadtetraacetate / α, α‐diniethyl alcohols
TY - 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 . .
