Reactions of linear conjugated dienone structures with arenes under superelectrophilic activation conditions. An experimental and theoretical study of intermediate multicentered electrophilic species

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Reactions of linear conjugated dienone structures with arenes under superelectrophilic activation conditions. An experimental and theoretical study of intermediate multicentered electrophilic species. / Kochurin, Matvei A.; Ismagilova, Alina R.; Zakusilo, Dmitriy N.; Khoroshilova, Olesya V.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.

In: New Journal of Chemistry, Vol. 46, No. 25, 23.05.2022, p. 12041-12053.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{e03bcbba737048acb151749b677f8c56,

title = "Reactions of linear conjugated dienone structures with arenes under superelectrophilic activation conditions. An experimental and theoretical study of intermediate multicentered electrophilic species",

abstract = "Reactions of linear conjugated dienone structures ArCH = CHCH CHC( O)X, 1,5-diarylpenta-2,4-dien-1-ones (X = Ar′), 5-phenylpenta-2,4-dienoic acid (Ar = Ph, X = OH) and its methyl ester (Ar = Ph, X = OMe), with arenes under superelectrophilic activation conditions by Br{\o}nsted superacids (CF3SO3H and FSO3H) or strong Lewis acid (AlCl3) result in the formation of various compounds, such as conjugated enones, indanes, and carbocyclic derivatives. The formation of the reaction products depends on the structures of starting compounds (dienone and arene) and on the reaction conditions (temperature, time, and medium acidity). In these transformations, starting dienones are precursors of di- and tri-centered electrophilic synthons leading to target products. A NMR study and DFT calculations have shown that the most probable reactive intermediates should be O,C-diprotonated species Ar+CHCH2CH CHC( O+H)X derived from the protonation of starting dienones. Plausible mechanisms of electrophilic transformations are discussed.",

author = "Kochurin, {Matvei A.} and Ismagilova, {Alina R.} and Zakusilo, {Dmitriy N.} and Khoroshilova, {Olesya V.} and Boyarskaya, {Irina A.} and Vasilyev, {Aleksander V.}",

note = "Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry",

year = "2022",

month = may,

day = "23",

doi = "10.1039/d2nj01828d",

language = "English",

volume = "46",

pages = "12041--12053",

journal = "New Journal of Chemistry",

issn = "1144-0546",

publisher = "Royal Society of Chemistry",

number = "25",

}

RIS

TY - JOUR

T1 - Reactions of linear conjugated dienone structures with arenes under superelectrophilic activation conditions. An experimental and theoretical study of intermediate multicentered electrophilic species

AU - Kochurin, Matvei A.

AU - Ismagilova, Alina R.

AU - Zakusilo, Dmitriy N.

AU - Khoroshilova, Olesya V.

AU - Boyarskaya, Irina A.

AU - Vasilyev, Aleksander V.

PY - 2022/5/23

Y1 - 2022/5/23

N2 - Reactions of linear conjugated dienone structures ArCH = CHCH CHC( O)X, 1,5-diarylpenta-2,4-dien-1-ones (X = Ar′), 5-phenylpenta-2,4-dienoic acid (Ar = Ph, X = OH) and its methyl ester (Ar = Ph, X = OMe), with arenes under superelectrophilic activation conditions by Brønsted superacids (CF3SO3H and FSO3H) or strong Lewis acid (AlCl3) result in the formation of various compounds, such as conjugated enones, indanes, and carbocyclic derivatives. The formation of the reaction products depends on the structures of starting compounds (dienone and arene) and on the reaction conditions (temperature, time, and medium acidity). In these transformations, starting dienones are precursors of di- and tri-centered electrophilic synthons leading to target products. A NMR study and DFT calculations have shown that the most probable reactive intermediates should be O,C-diprotonated species Ar+CHCH2CH CHC( O+H)X derived from the protonation of starting dienones. Plausible mechanisms of electrophilic transformations are discussed.

AB - Reactions of linear conjugated dienone structures ArCH = CHCH CHC( O)X, 1,5-diarylpenta-2,4-dien-1-ones (X = Ar′), 5-phenylpenta-2,4-dienoic acid (Ar = Ph, X = OH) and its methyl ester (Ar = Ph, X = OMe), with arenes under superelectrophilic activation conditions by Brønsted superacids (CF3SO3H and FSO3H) or strong Lewis acid (AlCl3) result in the formation of various compounds, such as conjugated enones, indanes, and carbocyclic derivatives. The formation of the reaction products depends on the structures of starting compounds (dienone and arene) and on the reaction conditions (temperature, time, and medium acidity). In these transformations, starting dienones are precursors of di- and tri-centered electrophilic synthons leading to target products. A NMR study and DFT calculations have shown that the most probable reactive intermediates should be O,C-diprotonated species Ar+CHCH2CH CHC( O+H)X derived from the protonation of starting dienones. Plausible mechanisms of electrophilic transformations are discussed.

UR - http://www.scopus.com/inward/record.url?scp=85131968882&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/743f509b-3342-38e8-92f3-0d955f459818/

U2 - 10.1039/d2nj01828d

DO - 10.1039/d2nj01828d

M3 - Article

AN - SCOPUS:85131968882

VL - 46

SP - 12041

EP - 12053

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 25

ER -

ID: 100073982