FORMATION OF BENZOCYCLOBUTEN-1-OL DERIVATIVES BY INTRAMOLECULAR CYCLIZATION OF O-ACYLBENZYLLITHIUMS

被引：11

作者：

KOBAYASHI, K

KAWAKITA, M

MANNAMI, T

KONISHI, H

机构：

[1] Department of Materials Science, Faculty of Engineering, Tottori University, Tottori

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 05期

关键词：

D O I：

10.1016/0040-4039(94)02328-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction between the carbanions, generated in situ bp the treatment of o-(trimethylsilylmethyl)phenyl ketones with lithium diisopropylamide (LDA). and chlorotrimethylsilane affords the corresponding 1-(trimethylsilyloxy)-2-trimethylsilylbenzocyclobutene derivatives. Alternatively, (o-lithiomethyl-o'-methoxy)phenyl ketones cyclize spontaneously or with an aid of chlorotrimethylsilane to give benzocyclobuten-1-ols or their trimethylsilyl ethers respectively.

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页码：733 / 736

页数：4

相关论文

共 16 条

[1] SYNTHESIS OF NATURAL-PRODUCTS VIA TERTIARY AZIDES, II, 2-ALKYL AND 2-ARYL INDOLES [J].

ADAM, G ;

ANDRIEUX, J ;

PLAT, M .

TETRAHEDRON LETTERS, 1981, 22 (33) :3181-3184

[2]

AIDEN IS, 1991, TETRAHEDRON LETT, V32, P2171

[3] METALATION OF ORTHO-HALOSTYRENE OXIDES - PREPARATION OF BENZOCYCLOBUTENOLS [J].

AKGUN, E ;

GLINSKI, MB ;

DHAWAN, KL ;

DURST, T .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (13) :2730-2734

[4]

CHARLTON JL, 1989, TETRAHEDRON LETT, V30, P3279

[5] DIELS-ALDER REACTIONS OF ALPHA-OXY-ORTHO-XYLYLENES [J].

CHOY, W ;

YANG, HL .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5796-5798

[6] STEREOSELECTIVITY IN THE DIELS-ALDER REACTION OF PHENYL-SUBSTITUTED AND OXY-SUBSTITUTED ORTHO-QUINODIMETHANES [J].

DURST, T ;

KOZMA, EC ;

CHARLTON, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (24) :4829-4833

[7] STEREOSELECTIVE SYNTHESIS OF AN ANALOG OF PODOPHYLLOTOXIN BY AN INTRAMOLECULAR DIELS-ALDER REACTION [J].

JUNG, ME ;

LAM, PY ;

MANSURI, MM ;

SPELTZ, LM .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (07) :1087-1105

[8] SYNTHESIS OF ORTHO-ACYLBENZYLBORONATES VIA CROSS-COUPLING REACTION OF (DIALKOXYBORYL)METHYLZINC REAGENTS WITH HALOARENES - A STABLE ORTHO-QUINODIMETHANE PRECURSOR [J].

KANAI, G ;

MIYAURA, N ;

SUZUKI, A .

CHEMISTRY LETTERS, 1993, (05) :845-848

[9] PHOTOINDUCED MOLECULAR-TRANSFORMATIONS .137. NEW GENERAL-SYNTHESIS OF 3-SUBSTITUTED 3,4-DIHYDRO-1H-BENZO[2]PYRAN-1-ONES (3,4-DIHYDROISOCOUMARINS) VIA RADICAL AND PHOTOCHEMICAL FRAGMENTATIONS AS THE KEY STEP [J].

KOBAYASHI, K ;

KONISHI, A ;

KANNO, Y ;

SUGINOME, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (01) :111-115

[10] PHOTOINDUCED MOLECULAR-TRANSFORMATIONS .89. A NEW SYNTHESIS OF PHTHALIDES THROUGH BETA-SCISSION OF BENZOCYCLOBUTENOL HYPOIODITES [J].

KOBAYASHI, K ;

ITOH, M ;

SUGINOME, H .

TETRAHEDRON LETTERS, 1987, 28 (29) :3369-3372