Synthesis and Oxidative Ring Contraction of 1,5,3,7-Dichalcogenadiazocanes. Novel Formation of 1,2,4-Diselenazolidines, 1,2,4-Ditellurazolidines, and 1,2,3,4,5,7-Pentathiazocanes

1,5,3,7-Dithiadiazocanes, 1,5,3,7-diselenadiazocanes, and 1,5,3,7-ditelluradiazocanes were prepared from a primary amine, formalin, and H2S, NaSeH, or NaTeH, respectively. Oxidation of 1,5,3,7-diselenadiazocanes and 1,5,3,7-ditelluradiazocanes using NBS efficiently afforded 1,2,4-diselenazolidines o...

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Published inBulletin of the Chemical Society of Japan Vol. 79; no. 12; pp. 1913 - 1925
Main Authors Takikawa, Yuji, Koyama, Yutaka, Yoshida, Takamasa, Makino, Kenshiro, Shibuya, Hiroki, Sato, Kazuto, Otsuka, Tatsuya, Shibata, Yuko, Onuma, Yuki, Aoyagi, Shigenobu, Shimada, Kazuaki, Kabuto, Chizuko
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 01.12.2006
Chemical Soc Japan
Chemical Society of Japan
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
CATION RADICALS
ORGANIC-SYNTHESIS
PERI-BRIDGED NAPHTHALENES
DITHIOETHER DICATIONS
DICHALCOGENA DICATIONS
HETEROCYCLES
S-SULFIDES
FACILE DEALKYLATION
TRIFLIC ANHYDRIDE
HYDROGEN-SULFIDE
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Summary:1,5,3,7-Dithiadiazocanes, 1,5,3,7-diselenadiazocanes, and 1,5,3,7-ditelluradiazocanes were prepared from a primary amine, formalin, and H2S, NaSeH, or NaTeH, respectively. Oxidation of 1,5,3,7-diselenadiazocanes and 1,5,3,7-ditelluradiazocanes using NBS efficiently afforded 1,2,4-diselenazolidines or 1,2,4-ditellurazolidines, respectively. In contrast, treatment of 1,5,3,7-dithiadiazocanes with bromine-elemental sulfur or disulfur dichloride (S2Cl2) afforded 1,2,3,4,5,7-pentathiazocanes. An unusual oxidative conversion of 1,5,3,7-dichalcogenadiazocanes into these products was assumed to proceed through in situ formation of 1,5,3,7-dichalcogenadiazabicyclo[3.3.0]octane-type dications.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.79.1913