Cyclopropane-shift type reaction of diaryl(2-halogenocyclopropyl)methanols promoted by Lewis acids

被引：14

作者：

Wakasugi, K

Nishii, Y

Tanabe, Y

机构：

[1] Kwansei Gakuin Univ, Sch Sci, Nishinomiya, Hyogo 6628501, Japan

[2] RIKEN, Inst Phys & Chem Res, Wako, Saitama 3510198, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 31期

基金：

日本学术振兴会;

关键词：

D O I：

10.1016/S0040-4039(00)00979-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel cyclopropane-shift type reaction of diaryl(2-halogenocyclopropyl)methanols 2b and 7 proceeded by using BF3. OEt2 and TiCl4, respectively. Utilizing these reactions, 1-aryl-3-chloro-1,2-methanoindans 5 and 9, 1-aryl-3-methylnaphthalenes 6, and 1,2-methano-1-arylindens 10 were constructed. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：5937 / 5942

页数：6

相关论文

共 13 条

[1] INVITRO CONVERSION OF HUMULENE TO DELTA-8(13)-CAPNELLENE - CYCLOPROPANE SLIDING REACTION [J].

FUJITA, T ;

OHTSUKA, T ;

SHIRAHAMA, H ;

MATSUMOTO, T .

TETRAHEDRON LETTERS, 1982, 23 (40) :4091-4094

[2]

HALTON B, 1987, CHEM CYCLOPROPYL GRO, P1223

[3] CHEMICAL CONVERSION OF HUMULENE TO DACTYLOL - BIOMIMETIC, APPARENT 1,2-SHIFT OF A METHYL-GROUP [J].

HAYASAKA, K ;

OHTSUKA, T ;

SHIRAHAMA, H ;

MATSUMOTO, T .

TETRAHEDRON LETTERS, 1985, 26 (07) :873-876

[4] ACID-CATALYZED REACTION OF DICHLOROCYCLOPROPYLCARBINOLS - PREPARATION OF 2-CYCLOPENTENONES [J].

HIYAMA, T ;

TSUKANAK.M ;

NOZAKI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (11) :3713-3714

[5] Stereoselective synthesis of cyclopropanes via homoallylic participation [J].

Nagasawa, T ;

Handa, Y ;

Onoguchi, Y ;

Suzuki, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (01) :31-39

[6]

Nishii Y, 1998, SYNLETT, P67

[7] Regiocontrolled benzannulation of diaryl(gem-dichlorocyclopropyl)methanols for the synthesis of ''unsymmetrically'' substituted alpha-arylnaphthalenes [J].

Nishii, Y ;

Yoshida, T ;

Tanabe, Y .

TETRAHEDRON LETTERS, 1997, 38 (41) :7195-7198

[8]

Patai S., 1987, The Chemistry of Cyclopropyl Group

[9] A NOVEL AND REGIOSELECTIVE RADICAL CYCLIZATION OF GEM-DIHALOCYCLOPROPYL SUBSTITUTED ALKENES AND ALKYNES USING TRIBUTYLTIN HYDRIDE AND CATALYTIC AIBN [J].

TANABE, Y ;

NISHII, Y ;

WAKIMURA, K .

CHEMISTRY LETTERS, 1994, (09) :1757-1760

[10] Synthetic study on the utilization of gem-dihalo- and halocyclopropanes:: Cationic approach toward versatile and highly selective benzannulations [J].

Tanabe, Y ;

Nishii, Y .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1999, 57 (03) :170-180