β-trifluoroacetylvinyl phenyl sulfoxide -: synthesis, Diels-Alder reaction and computational study

被引：7

作者：

Krasovsky, AL ^{[1
]}

Pissarev, SA ^{[1
]}

Nenajdenko, VG ^{[1
]}

Balenkova, ES ^{[1
]}

机构：

[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119899, Russia

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 22期

关键词：

D O I：

10.1039/b202583c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Diels-Alder reaction of sulfoxide 2 with 1,3-dienes in CH2Cl2 afforded the corresponding CF3-containing mono- and polycycloadducts. In the case of the reaction of sulfoxide 2 and sulfonium salt 10 with cyclopentadiene, a mixture of four diastereomers was formed. The rotational potential energy surface ( PES) of reagents 2, 10 was calculated and gave three minimum energy conformations with S=O, Ph or the lone pair synperiplanar to the carbon-carbon double bond.

引用

页码：2554 / 2560

页数：7

共 50 条

[1] STUDY ON DIELS-ALDER REACTION
CORTES, L
PAYO, E
ROJAS, A
MONASTER.J
ACEVEDO, S
ACTA CIENTIFICA VENEZOLANA, 1970, 21 : 75 - &
[2] SYNTHESIS OF MULTISTRIATINS BY DIELS-ALDER REACTION
MORI, Y
INABA, M
SUZUKI, M
KONISHI, H
JOURNAL OF PHARMACEUTICAL SCIENCES, 1987, 76 (11) : S241 - S241
[3] The Diels-Alder Reaction in Steroid Synthesis
Mackay, Emily G.
Sherburn, Michael S.
SYNTHESIS-STUTTGART, 2015, 47 (01): : 1 - 21
[4] USE OF PHENYL VINYL SULFOXIDE AS AN ACETYLENE EQUIVALENT IN DIELS-ALDER CYCLOADDITIONS
PAQUETTE, LA
MOERCK, RE
HARIRCHIAN, B
MAGNUS, PD
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (05) : 1597 - 1599
[5] DIELS-ALDER REACTION IN POLYMER SYNTHESIS
STILLE, JK
HARRIS, FW
MUKAMAL, H
RAKUTIS, RO
SCHILLIN.CL
NOREN, GK
REED, JA
ADVANCES IN CHEMISTRY SERIES, 1969, (91): : 628 - &
[6] The Diels-Alder reaction in total synthesis
Nicolaou, KC
Snyder, SA
Montagnon, T
Vassilikogiannakis, G
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (10) : 1668 - 1698
[7] The Diels-Alder reaction in total synthesis
Nicolaou, K.C.
Snyder, Scott A.
Montagnon, Tamsyn
Vassilikogiannakis, Georgios
1668, Wiley-VCH Verlag (41)
[8] β-Trifluoromethylated nitroethenes in Diels-Alder reaction with cyclopentadiene: A DFT computational study
Jasinski, Radomir
JOURNAL OF FLUORINE CHEMISTRY, 2018, 206 : 1 - 7
[9] Strained allenes as dienophiles in the Diels-Alder reaction: An experimental and computational study
Nendel, M
Tolbert, LM
Herring, LE
Islam, MN
Houk, KN
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03): : 976 - 983
[10] Diels-Alder reaction involving an unusual dienophile: Computational and mechanistic study
Waas, Jack R.
Singleton, Daniel A.
Besinaiz, Jacqueline O.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233

← 1 2 3 4 5 →