Rearrangement of Substituted 2,4,4,6-Tetraaryl-4H-thiopyrans to Triaryl-3aH-benzo[3,4]cyclopenta[1,2-b]thiophene

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Title:Rearrangement of Substituted 2,4,4,6-Tetraaryl-4H-thiopyrans to Triaryl-3aH-benzo[3,4]cyclopenta[1,2-b]thiophene
Creators:
Kroulík, Jiří
Čejka, Jan
Sedmera, Petr
Jegorov, Alexandr
Kratochvíl, Bohumil
Kuthan, Josef
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 8, pp. 1631-1642
Uncontrolled Keywords:Thiapentalene, Benzo[3,4]cyclopenta[1,2-<i>b</i>]thiophene, Rearrangements, Bromination, Thiopyrans, Sulfur heterocycles

Abstract

An intensive bromination of 2,6-diaryl-4,4-diphenyl-4<i>H</i>-thiopyrans can lead through 3,5-dibromo derivatives to unexpected 2,8-diaryl-3-bromo- and 2,8-diaryl-3,5-dibromo-3a-phenyl-3a<i>H</i>-benzo[3,4]cyclopenta[1,2-<i>b</i>]thiophene as demonstrated on examples where the respective aryl groups are phenyl or 4-fluorophenyl. On the other hand, analogous spiro- [fluorene-9,4'-thiopyran]s do not exhibit the rearrangement evidently due to a rigid conformation of the fluorene moiety. The reaction mechanism for the rearrangement is proposed. <p>

Title:Rearrangement of Substituted 2,4,4,6-Tetraaryl-4H-thiopyrans to Triaryl-3aH-benzo[3,4]cyclopenta[1,2-b]thiophene
Creators:
Kroulík, Jiří
Čejka, Jan
Sedmera, Petr
Jegorov, Alexandr
Kratochvíl, Bohumil
Kuthan, Josef
Uncontrolled Keywords:Thiapentalene, Benzo[3,4]cyclopenta[1,2-<i>b</i>]thiophene, Rearrangements, Bromination, Thiopyrans, Sulfur heterocycles
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:69
Number:8
Page Range:pp. 1631-1642
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20041631UNSPECIFIED
ID Code:2299
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Kroulík, Jiří; Čejka, Jan; Sedmera, Petr; Jegorov, Alexandr; Kratochvíl, Bohumil; Kuthan, Josef (2004) Rearrangement of Substituted 2,4,4,6-Tetraaryl-4H-thiopyrans to Triaryl-3aH-benzo[3,4]cyclopenta[1,2-b]thiophene. Collection of Czechoslovak Chemical Communications, 69 (8). pp. 1631-1642. ISSN 0010-0765

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