CYCLIZATION REACTIONS OF MOLYBDENUM AND CHROMIUM CARBENE COMPLEXES WITH 1,6-ENYNES AND 1,7-ENYNES - EFFECT OF TETHER LENGTH AND COMPOSITION

被引:55
|
作者
HARVEY, DF
LUND, KP
NEIL, DA
机构
[1] Department of Chemistry, University of California, San Diego, California 92093-0506, La Jolla
关键词
D O I
10.1021/ja00048a012
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
It has been observed that the reaction of 1,6- and 1,7-enynes with pentacarbonyl(butylmethoxycarbene)molybdenum(0) (18) produces vinylcyclopropanes in good to excellent yield. A systematic investigation into the factors which govern the success of these cyclizations has been performed. Chromium carbene complexes also lead to the formation of vinylcyclopropanes but in significantly lower yields. When the pathway to vinylcyclopropanes is not followed, a number of other distinct types of products are obtained. The pathways leading to these various products are discussed and compared.
引用
收藏
页码:8424 / 8434
页数:11
相关论文
共 50 条
  • [21] Chiral carbene approach to gold-catalyzed asymmetric cyclization of 1,6-enynes
    Matsumoto, Yasumasa
    Selim, Khalid B.
    Nakanishi, Hirotsugu
    Yamada, Ken-ichi
    Yamamoto, Yasutomo
    Tomioka, Kiyoshi
    TETRAHEDRON LETTERS, 2010, 51 (02) : 404 - 406
  • [22] Ruthenium-catalyzed cycloisomerizations of 1,6- and 1,7-enynes
    Trost, BM
    Toste, FD
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (04) : 714 - 715
  • [23] Iron-Catalyzed Reductive Cyclization of 1,6-Enynes
    Lin, Aijun
    Zhang, Zhi-Wei
    Yang, Jiong
    ORGANIC LETTERS, 2014, 16 (02) : 386 - 389
  • [24] Cobalt-Catalyzed Hydrosilylation/Cyclization of 1,6-Enynes
    Xi, Tuo
    Lu, Zhan
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19): : 8858 - 8866
  • [25] Iron-Catalyzed Hydroborylative Cyclization of 1,6-Enynes
    Cabrera-Lobera, Natalia
    Rodriguez-Salamanca, Patricia
    Nieto-Carmona, Juan C.
    Bunuel, Elena
    Cardenas, Diego J.
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (04) : 784 - 788
  • [26] Pd-catalyzed borylative cyclization of 1,6-enynes
    Marco-Martinez, Juan
    Lopez-Carrillo, Veronica
    Bunuel, Elena
    Simancas, Raquel
    Cardenas, Diego J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (07) : 1874 - +
  • [27] PtCl4-catalyzed cycloreorganization of 1,6-and 1,7-enynes
    Oh, CH
    Bang, SY
    Rhim, CY
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2003, 24 (07) : 887 - 888
  • [28] Dinuclear-gold-catalyzed cyclization of 1,7-enynes with alkyl bromides
    Li, Jiajun
    Zhai, Xinyi
    Ji, Cheng-Long
    Li, Weipeng
    Xie, Jin
    CHEMICAL COMMUNICATIONS, 2023, 59 (51) : 7943 - 7946
  • [29] Visible-Light Mediated Diarylselenylative Cyclization of 1,6-Enynes
    Hou, Hong
    Sun, Yue
    Pan, Yingjie
    Yu, Huaguang
    Han, Ying
    Shi, Yaocheng
    Yan, Chaoguo
    Zhu, Shaoqun
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 1273 - 1280
  • [30] Regiodivergent hydrosilylation in the nickel(0)-catalyzed cyclization of 1,6-enynes
    Bai, Dachang
    Cheng, Ruoshi
    Yang, Jiaxin
    Xu, Wenjie
    Chen, Xingge
    Chang, Junbiao
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (19) : 5285 - 5291