Synthesis of new 10,11-dihydrodibenzo[a,d]cycloheptene S-thiocarbamate derivatives via a benzylic Newman–Kwart rearrangement

New S-thiocarbamates possessing a 10,11-dihydro-5H-dibenzo[a,d]cycloheptene moiety were obtained unexpectedly in the process of preparing new O-thiocarbamates starting from 5-dibenzosuberol (10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol) and aroyl-isothiocyanates. These compounds were obtained via a...

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Published inTetrahedron letters Vol. 55; no. 29; pp. 4011 - 4013
Main Authors Căproiu, Miron Teodor, Dumitrascu, Florea, Shova, Sergiu, Chirită, Ileana Cornelia, Missir, Alexandru Vasile, Cioroianu, Dana-Mihaela
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 16.07.2014
Elsevier
Subjects
10,11-Dihydro-5H-dibenzo[a,d]cycloheptene
Chemistry
Chemistry, Organic
Crystallography
Derivatives
Infrared radiation
Newman–Kwart rearrangement
NMR spectroscopy
O-Thiocarbamates
Physical Sciences
S-Thiocarbamates
Science & Technology
Synthesis (chemistry)
Tetrahedrons
X-rays
Newman–Kwart rearrangement
10,11-Dihydro-5H-dibenzo[a,d]cycloheptene
S-Thiocarbamates
O-Thiocarbamates
ACID
Newman-Kwart rearrangement
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Summary:New S-thiocarbamates possessing a 10,11-dihydro-5H-dibenzo[a,d]cycloheptene moiety were obtained unexpectedly in the process of preparing new O-thiocarbamates starting from 5-dibenzosuberol (10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol) and aroyl-isothiocyanates. These compounds were obtained via a benzylic Newman–Kwart rearrangement mechanism. The structures of the new thiocarbamates were confirmed by elemental analysis, IR, and NMR spectroscopy and by X-ray crystallography.
Bibliography:ObjectType-Article-1
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ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.05.088