Reactions of guaiazulene with 2-furaldehyde, thiophene-2-carbaldehyde and pyrrole-2-carbaldehyde in methanol in the presence of hexafluorophosphoric acid: comparative studies on molecular structures and spectroscopic, chemical and electrochemical properties of monocarbocations stabilized by 3-guaiazulenyl and 2-furyl (or 2-thienyl or 2-pyrrolyl) groups

被引：23

作者：

Takekuma, S

Takahashi, K

Sakaguchi, A

Shibata, Y

Sasaki, M

Minematsu, T

Takekuma, H

机构：

[1] Kinki Univ, Fac Sci & Engn, Dept Appl Chem, Osaka 5778502, Japan

[2] Kinki Univ, Sch Pharmaceut Sci, Osaka 5778502, Japan

来源：

TETRAHEDRON | 2005年 / 61卷 / 43期

关键词：

carbenium ions; electrochemistry; furan; guaiazulene; pyrrole; reduction; thiophene; X-ray crystal structures;

D O I：

10.1016/j.tet.2005.07.104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of guaiazulene (1) with heteroaromatic-carbaldehydes [i.e., 2-furaldehyde (2), thiophene-2-carbaidehyde (3) and pyrrole-2-carbaldehyde (4)] in methanol in the presence of hexafluorophosphoric acid at 25 degrees C for 30 min under aerobic conditions give (2-furyl)(3-guaiazulenyl)methylium hexafluorophosphate (5), (3-guaiazulenyl)(2-thienyl)methylium hexafluorophosphate (6) and (3-guaiazulenyl)(2-pyrrolyl)methylium hexafluorophosphate (7), respectively, in 93, 98 and 85% yields. Comparative studies on the molecular structures as well as the spectroscopic, chemical and electrochemical properties of the methylium hexafluorophosphates 5-7 stabilized by 3-guaiazulenyl and 2-furyl (or 2-thienyl or 2-pyrrolyl) groups are reported. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：10349 / 10362

页数：14

共 3 条

[1] Reactions of guaiazulene with methyl terephthalaldehydate and 2-hydroxy- and 4-hydroxybenzaldehydes in methanol in the presence of hexafluorophosphoric acid: comparative studies on molecular structures and spectroscopic, chemical and electrochemical properties of monocarbocations stabilized by 3-guaiazulenyl and phenyl groups
Takekuma, S
Hata, Y
Nishimoto, T
Nomura, E
Sasaki, M
Minematsu, T
Takekuma, H
TETRAHEDRON, 2005, 61 (28) : 6892 - 6907
[2] Preparation, molecular structures, and characteristic properties of (E)-1-(2-furyl)- and (E)-1-(2-thienyl)-2-(3-guaiazulenyl)ethylenes and (E)-1-(3-furyl)- and (E)-1-(3-thienyl)-2-(3-guaiazulenyl)ethylenes
Takekuma, Shin-ichi
Nagata, Keisuke
Yoshioka, Yusuke
Obata, Hironori
Minami, Takaharu
Tanaka, Tomoyoshi
Yashima, Keisuke
Minematsu, Toshie
Takekuma, Hideko
TETRAHEDRON, 2012, 68 (33) : 6737 - 6758
[3] Reactions of (1R,2S)-1,2-di(2-furyl)-1,2-di(3-guaiazulenyl)ethane and (1R,2S)-1,2-di(3-guaiazulenyl)-1,2-di(2-thienyl)ethane with tetracyanoethylene (TCNE) in benzene:: comparative studies on the products and their spectroscopic properties
Takekuma, S
Takahashi, K
Sakaguchi, A
Sasaki, M
Minematsu, T
Takekuma, H
TETRAHEDRON, 2006, 62 (07) : 1520 - 1526

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