An Efficient Synthesis of Terminal Allenes from Terminal 1-Alkynes

被引：153

作者：

Kuang, Jinqiang

Ma, Shengming ^{[1
]}

机构：

[1] E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Dept Chem, Shanghai 200062, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 04期

基金：

中国国家自然科学基金;

关键词：

CATALYZED REACTIONS; PROPARGYLIC AMINES; CYCLIZATION; ARYL; 3,4-ALLENOLS; ALCOHOLS; HALIDES; KETONES; ALKYNES;

D O I：

10.1021/jo802391x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a modified method for the synthesis of terminal allenes from terminal 1-alkyne: The reaction of 1-alkynes with 1.8 equiv of Cy2NH and 2.5 equiv of paraformaldehyde mediated by CuI (0.5 equiv) in refluxing dioxane may produce terminal allenes in much higher yields than the previously reported protocol and many functional groups such as mesylate, hydroxyl group, ether, amide, etc. may be tolerated.

引用

页码：1763 / 1765

页数：3

共 41 条

[31] INDIRECT ELECTROREDUCTIVE CYCLIZATION OF N-ALLYLIC AND N-PROPARGYLBROMO AMIDES AND O-BROMOACRYLOYLANILIDES USING NICKEL(II) COMPLEXES AS ELECTRON-TRANSFER CATALYSTS [J].

OZAKI, S ;

MATSUSHITA, H ;

OHMORI, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (19) :2339-2344

[32] A NOVEL SYNTHESIS OF SUBSTITUTED ALLENES [J].

RONA, P ;

CRABBE, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (12) :3289-&

[33] OBSERVATION ON THE SYNTHESIS OF ALLENES BY HOMOLOGATION OF ALK-1-YNES [J].

SEARLES, S ;

LI, Y ;

NASSIM, B ;

LOPES, MTR ;

TRAN, PT ;

CRABBE, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (04) :747-751

[34]

SPEICHER A, 1996, PRAKT CHEMIE, V338, P558

[35] Allenes from cyclopropanes and their use in organic synthesis - Recent developments [J].

Sydnes, LK .

CHEMICAL REVIEWS, 2003, 103 (04) :1133-1150

[36] INTRAMOLECULAR DIELS-ALDER REACTIONS OF 1,2,4-TRIAZINES - SYNTHESIS OF 2,3-CYCLOPENTENOPYRIDINES AND 5,6,7,8-TETRAHYDROQUINOLINES [J].

TAYLOR, EC ;

MACOR, JE ;

FRENCH, LG .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1807-1812

[37] Cationic cyclopentannelation of allene ethers [J].

Tius, MA .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :284-290

[38] Rapid and solvent-free synthesis of homoallyl or homopropargyl alcohols mediated by zinc powder [J].

Wang, JX ;

Jia, XF ;

Meng, TJ ;

Xin, L .

SYNTHESIS-STUTTGART, 2005, (17) :2838-2844

[39] Cascade radical cyclizations via biradicals generated from enediynes, enyne-allenes, and enyne-ketenes [J].

Wang, KK .

CHEMICAL REVIEWS, 1996, 96 (01) :207-222

[40] The emergence of allenamides in organic synthesis [J].

Wei, LL ;

Xiong, H ;

Hsung, RP .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (10) :773-782

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