Reaction of o‐Carboryne with Furans: Facile Synthesis of Carborane‐ Fused Oxanorbornenes and Their Derivatives

o‐Carboryne (1,2‐dehydro‐o‐carborane) is a very useful synthon for the synthesis of a variety of carborane‐functionalized molecules. Diels‐Alder reaction of o‐carboryne with furans gave a series of carborane‐fused oxanorbornenes in moderate to high yields using 1‐OTf‐1,2‐C2B10H11 as carboryne precur...

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Published inChinese journal of chemistry Vol. 36; no. 4; pp. 273 - 279
Main Authors Zhang, Rongyi, Yuan, Yinggen, Qiu, Zaozao, Xie, Zuowei
Format Journal Article
LanguageEnglish
Published Weinheim WILEY‐VCH Verlag GmbH & Co. KGaA 01.04.2018
Wiley Subscription Services, Inc
Subjects
[4 + 2] cycloaddition
Bromination
Carborane
carboryne
Chemical synthesis
Cycloaddition
furan
Furans
Materials science
Oxidation
Pesticides
Ring opening
ring opening reaction
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Summary:o‐Carboryne (1,2‐dehydro‐o‐carborane) is a very useful synthon for the synthesis of a variety of carborane‐functionalized molecules. Diels‐Alder reaction of o‐carboryne with furans gave a series of carborane‐fused oxanorbornenes in moderate to high yields using 1‐OTf‐1,2‐C2B10H11 as carboryne precursor. The resultant cycloadducts can undergo hydrogenation, cyclic oxidation, bromination, [4 + 2]/[2 + 2] cycloaddition and nucleophilic ring opening reaction to afford a variety of highly functionalized carboranes that may find applications as useful basic units in medicine and materials science. Reaction of o‐carboryne with furans gives [4 + 2] cycloadducts, which can be converted to [2 + 2] cycloadducts, 1‐furanyl‐o‐carboranes and other multifunctionalized carboranes.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201700772