Regioselective synthesis of substituted bicyclo[3.2.1]oct‐3‐ene‐2,8‐diones via double carbonylation of 1,3‐cyclohexadienes | Zendy

Eilbracht Peter | Zendy; Jelitte Rüdiger | Zendy; Trabold Peter | Zendy

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Regioselective synthesis of substituted bicyclo[3.2.1]oct‐3‐ene‐2,8‐diones via double carbonylation of 1,3‐cyclohexadienes

Author(s) -

Eilbracht Peter,

Jelitte Rüdiger,

Trabold Peter

Publication year - 1986

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19861190117

Subject(s) - chemistry , bicyclic molecule , regioselectivity , carbonylation , diketone , stereochemistry , medicinal chemistry , double bond , carbon monoxide , organic chemistry , catalysis

Double carbonylation of 1,3‐cyclohexadienes 1 is applied to the synthesis of substituted bicyclo[3.2.1]oct‐3‐ene‐2,8‐diones 4 . The Lewis acid mediated ring enlargement of substituted cyclohexadiene complexes 2 produces the cycloheptanone alkyl allyl complexes 3 with high regioselectivity. Substituted bicyclic diketones 4 are obtained in high yields by treating the complexes 3 with carbon monoxide under pressure or by oxidative decomposition. The two carbonylation steps can also be performed in a one‐pot version.

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