104281-70-1Relevant academic research and scientific papers
Allylic nitro compounds as nitrite donors
Chakrapani, Harinath,Gorczynski, Michael J.,King, S. Bruce
, p. 16332 - 16337 (2006)
Allylic nitro compounds were synthesized and evaluated as organic sources of nitrite and nitric oxide. Unactivated allylic nitro compounds do not spontaneously release nitrite and nucleophile promoted nitrite release is slow. However, 2-(nitromethyl)-cycl
Stereo- and Regio-chemical Control in Phenylthio Migration around Rings of Sizes 5-15
Hannaby, Malcolm,Judson, Philip,Warren, Stuart
, p. 2609 - 2614 (2007/10/02)
Acid-catalysed rearrangement of cyclic alcohols with neighbouring syn or anti phenylthio groups leads to allylic sulfides with endo- or exo-cyclic double bonds.Only the anti alcohols rearrange for ring sizes n=5-10 but the syn alcohol rearranges if n=12 o
Preparation of allylic lithium reagents with the allylic system partly incorporated into carbocyclic rings
Screttas, Constantinos G.,Smonou, Ioulia C.
, p. 143 - 152 (2007/10/02)
A new method is described for preparation of allylic type organolithiums in which two of the allylic system carbons form part of carbocyclic ring.It involves cleavage of the readily accessible allylic sulfides 1-phenylthiomethylcycloalkanes by the naphthalenelithium in tetrahydrofuran.Carbonation of the reagents has given mixtures of cycloalken-1-yl acetic acids and 2-methylecycloalkane carboxylic acids, the distribution of which is strongly dependent on the ring size; thus the proportion of cycloalkenyl acetic acid, the endocyclic olefinic product, increases sharply on going from C5 to C8 ring derivatives and then considerably less sharply on going from C8 to C10 at which point the carbonation reaction has a high selectivity.It is concluded that the site of attack in the allylic anion by CO2 is determined by the thermochemical stability of the product(s).
A Novel Method for Furan Annelation by the Regioselective Acylation of Allylic Sulfides via α-Silyl Intermediates
Hiroi, Kunio,Sato, Hiroyasu
, p. 811 - 814 (2007/10/02)
Aluminum chloride-catalyzed acylations of allylic phenyl sulfides 3 with acid chlorides 5 were carried out via α-silyl intermediates 4 to give γ-acylated vinylic sulfides 6 with complete regioselectivity.Treatment of the γ-acylated compounds with concentr
Acid-Catalyzed Regioselective Acylation of α-Silylallylic Sulfides and Its Application to a Novel Cyclopentannelation and Furan Annelation
Hiroi, Kunio,Sato, Hiroyasu,Chen, Lih-Ming,Kotsuji, Kumiko
, p. 1413 - 1426 (2007/10/02)
Introduction of a silyl group at the α-position of allylic sulfides, followed by the aluminum chloride-catalyzed reaction of the resulting α-silylallylic sulfides with acid chlorides resulted in regioselective acylation at the γ-position of the allylic system to give γ-acylated vinylic sulfides, chemically equivalent to 1,4-dicarbonyl compounds.Heating of the products in refluxing benzene with an equimolar amount of p-toluenesulfonic acid produced 2-cyclopentanone derivatives.Treatment of the acylated products with an equimolar amount of concentrated sulfuric acid gave α-phenylthiofuran derivatives.These procedures provide a novel method for cyclopentannelation and furan annelation.Keywords - α-silylallylic sulfide; acid chloride; aluminum chloride; acid-catalyzed acylation; vinylic sulfide; 2-cyclopentanone; α-phenylthiofuran; furan; cyclopentannelation; furan annelation
REARRANGEMENT OF CYCLIC ALCOHOLS WITH AN ADJACENT PHENYLTHIO (PhS-) GROUP: MIGRATION OF A PhS GROUP AROUND A RING.
Hannaby, Malcolm,Warren, Stuart
, p. 765 - 768 (2007/10/02)
PhS migratoin around rings (size 5-15) gives allyl sulphides with a regioselectivity wich varies with ring size.
