Chemoselective Strain Release of Bicyclo[1.1.1]pent-1-yl Alcohols

被引：0
|
作者：
Ma, Yue [1 ]
Ai, Yinan [1 ]
Yu, Songjie [1 ,2 ]
机构：
[1] Dalian Univ Technol, Zhang Dayu Sch Chem, Dalian 116024, Peoples R China
[2] Shandong Univ, Inst Mol Sci & Engn, Inst Frontier & Interdisciplinary Sci, Qingdao 266237, Peoples R China
来源：
SYNLETT | 2023年 / 34卷 / 04期
关键词：
bicyclopentyl alcohols; strain release; C-C bond cleavage; chemoselectivity; cyclobutanones; enones; C-C BOND; CYCLOBUTANOLS REGIOSPECIFIC SYNTHESIS; TERT-CYCLOBUTANOLS; CLEAVAGE; CYCLOPROPANOLS; BENZOCYCLOBUTENOLS; CYCLOALKANOLS; ACTIVATION; GENERATION; AMINATION;
D O I：
10.1055/a-1992-6707
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The chemoselective C-C bond cleavage of bicyclo[1.1.1]pent-1-yl alcohols (BCP-OHs) was examined. Highly ring strained BCP-OHs were found to be particularly reactive, delivering cyclobutanone derivatives through a base-mediated single C-C bond cleavage or ?,?-unsaturated ketones by palladium-catalyzed dual C-C bond cleavage.
引用
收藏
页码：359 / 363
页数：5
相关论文
共 24 条
  • [21] Cooperativity in spin crossover materials as ligand's responsibility - investigations of the Fe(II)-1,3-bis((1H-tetrazol-1-yl)methyl)bicyclo[1.1.1]pentane system
    Knoll, Christian
    Mueller, Danny
    Seifried, Marco
    Giester, Gerald
    Welch, Jan M.
    Artner, Werner
    Hradil, Klaudia
    Reissner, Michael
    Weinberger, Peter
    DALTON TRANSACTIONS, 2018, 47 (16) : 5553 - 5557
  • [22] A practical metal-free homolytic aromatic alkylation protocol for the synthesis of 3-(pyrazin-2-yl)bicyclo[1.1.1]pentane-1-carboxylic acid
    Thirumoorthi, Navanita T.
    Adsool, Vikrant A.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (40) : 9485 - 9489
  • [23] SOLVOLYSES OF BICYCLO[2.2.2]OCT-1-YL AND 1-ADAMANTYL SYSTEMS CONTAINING AN ETHYLIDENE SUBSTITUENT ON THE 2-POSITION - TYPICAL EXAMPLES OF RATE ENHANCEMENTS ASCRIBED TO RELIEF OF F-STRAIN
    OHGA, Y
    MUNAKATA, M
    KITAGAWA, T
    KINOSHITA, T
    TAKEUCHI, K
    OISHI, Y
    FUJIMOTO, H
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15): : 4056 - 4067
  • [24] EVIDENCE OF PREVAILING STRAIN EFFECTS ON THE VALENCE STATE OF THE 5-PHENYL-4,6-DIOXA-1-AZA-5-PHOSPHA(V)BICYCLO[3.3.0]OCTAN-5-YL RADICAL
    HAMERLINCK, JHH
    SCHIPPER, P
    BUCK, HM
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (07) : 350 - 351
123