Reaction of alkynes with iodine monochloride revisited

被引：48
作者：
Bellina, F
Colzi, F
Mannina, L
Rossi, R
Viel, S
机构：
[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
[2] Univ Molise, Fac Sci MFN, I-86170 Isernia, Italy
[3] CNR, Area Ric Roma Montelibretti, Ist Metodol Chim, I-00016 Monterotondo, Roma, Italy
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 26期
关键词：
D O I：
10.1021/jo035372f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
6-Exo-dig and/or 7-endo-dig iodocyclization reactions of functionalized acetylenic derivatives with ICI are disfavored in comparison with the corresponding electrophilic addition reactions providing regioselectively (E)-1-chloro-2-iodoethene derivatives. On the contrary, 6-endo-dig and 5-exo-dig iodocyclizations of methyl ynoates with ICI seem to be favored in comparison with the corresponding electrophilic addition reactions.
引用
收藏
页码：10175 / 10177
页数：3
相关论文
共 26 条
[1]   HALOGENATION OF ALKYNES AND ALKYNYLSILANES [J].
ALHASSAN, MI .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 372 (02) :183-186
[2]  
ANDERSSON K, 1972, CHEM SCRIPTA, V2, P117
[3]   RULES FOR RING-CLOSURE [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736
[4]   REACTIVITY OF VINYL SULFONIC ESTERS .14. ADDITION OF TRINITROBENZENESULFONYL HYPOHALITES TO ACETYLENE DERIVATIVES TO GIVE BETA-HALOGENOVINYL SULFONATES [J].
BASSI, P ;
TONELLAT.U .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (07) :669-673
[5]  
Biagetti M, 2002, EUR J ORG CHEM, V2002, P1063, DOI 10.1002/1099-0690(200203)2002:6<1063::AID-EJOC1063>3.0.CO
[6]  
2-M
[7]   New procedures for the selective synthesis of 2(2H)-pyranone derivatives and 3-aryl-4-iodoisocoumarins [J].
Biagetti, M ;
Bellina, F ;
Carpita, A ;
Stabile, P ;
Rossi, R .
TETRAHEDRON, 2002, 58 (25) :5023-5038
[8]  
Claridge T. D. W., 1999, HIGH RESOLUTION NMR, P303
[9]  
DEBON A, 1975, B SOC CHIM FR II-CH, P2493
[10]  
FRIEBOLIN H, 1991, BASIC 1 2 DIMENSIONA, P56
123