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Synthesis 2002(10): 1355-1358
DOI: 10.1055/s-2002-33104
PAPER
© Georg Thieme Verlag Stuttgart · New York

First Synthesis of Thiocarbonyl Derivatives of Cage Ketones

Jaroslaw Romański*, Grzegorz Mlostoń
University of Łódź, Section of Heteroorganic Compounds, Narutowicza 68, 90-136 Łódź, Poland
e-Mail: romanski@krysia.uni.lodz.pl;
Further Information

Publication History

Received 2 January 2002
Publication Date:
01 August 2002 (online)

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Abstract

Thionation of pentacyclo[5.4.0.0 [2] [6] .0 [3] [10] .0 [5] [8] ]undecane-8-one (2) with P2S5 in pyridine afforded the corresponding thione 7 in good yield (70%). In contrast to this result, the P2S5 promoted thionation of pentacyclo[5.4.0.0 [2] [6] .0 [3] [10] .0 [5] [8] ]undecane-8,11-dione (1) did not afford the expected dithiocarbonyl derivative. Alternatively, reaction of methanolic 1 with H2S(g)/HCl(g) led to the thiocarbonyl­ derivatives 8 and 9. At longer reaction times (3-5 h), this reaction afforded two unexpected products 10 and 11, both of which are 3,5-disubstituted-4-thiahexacyclo[5.4.1.0 [2] [6] .0 [3] [10] .0 [5] [9] ]-dodecanes.

Key words

cage ketones - thioketones synthesis - sulfur derivative

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