81576-35-4Relevant academic research and scientific papers
ELECTROPHILIC SULFAMATOSULFENYLATION OF OLEFINS
Zefirov, N.S.,Zyk, N.V.,Kutateladze, A.G.,Lapin, Yu.A.
, p. 351 - 360 (2007/10/02)
The reaction of N,N-dialkylarenesufenamides with sulfur trioxides gave arenesulfenyl sulfamates, which have clearly defined electrophilic characteristics.These reagents are capable of adding at the C=C bond of olefins with the formation of the sulfamates of arylthio-substituted alcohols.The reaction with cyclohexene is stereospecific and leads to the trans-1,2-adducts, while the reaction with norbornene and norbornadiene is accompanied by rearrangement of the carbon framework.For the case of the cyclohexane derivatives it was shown that the vicinal arylthiosulfamates are highly sensitive to nucleophilic reagents.
Ring Contractions of Thiochroman-4-ones and Thiochromen-4-ones
MacKenzie, Neil E.,Thomson, Ronald H.
, p. 395 - 402 (2007/10/02)
3-Bromothiochroman-4-one and its S-oxide undergo ring contraction on heating, especially in the presence of sodium acetate, to give mixtures which include thioindigo (9) and the ethanediylidenethioindigo (10).Brominated 2,2-dimethylthiochroman-4-one reacts on silica gel to form thioindigo, thioindirubin, and the bis(benzothieno)pyran (17).Bromination of thiochromanone gives a number of products, including 2,3-dibromothiochromen-4-one S-oxide which, on heating with sodium acetate in acetic acid, is converted efficiently into thioindigo.The mechanism of this reaction is investigated.
