61829-44-5Relevant articles and documents
Allylic nitro compounds as nitrite donors
Chakrapani, Harinath,Gorczynski, Michael J.,King, S. Bruce
, p. 16332 - 16337 (2007/10/03)
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
Synthesis of Cyclic Allylic Sulphides (Ring Sizes 5-15) via Phenylthio Participation
Hannaby, Malcolm,Warren, Stuart
, p. 303 - 311 (2007/10/02)
Dehydration of β-phenylthio alcohols occurs with PhS participation unless stereochemistry prevents it.Without PhS participation, mixtures of allylic and vinylic sulphides are formed, but with PhS participation routes to three families of cyclic allylic su
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).
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.
DEHYDRATION OF ALCOHOLS WITH AN ADJACENT PHENYLTHIO (PhS) GROUP
Hannaby, Malcolm,Warren, Stuart
, p. 3133 - 3136 (2007/10/02)
Rings produce particular constraints not experienced by acyclic systems.We have investigated how the change in conformational and steric factors caused by varying the ring size affects a reaction within cyclic systems.
Direct Conversion of Allylic Nitro Compounds into Allyl Sulphides and Allyl Sulphones
Ono, Noboru,Hamamoto, Isami,Yanai, Tetsuya,Kaji, Aritsune
, p. 523 - 524 (2007/10/02)
Allylic nitro compounds are directly converted into allyl sulphides or allyl sulphones with high regioselectivity on treatment with sodium benzenethiolate alone or with sodium benzenesulphinate in the presence of a catalytic amount of Pd(PPh3)4.
Synthesis of Allyl Thioethers
Giese, Bernd,Mazumdar, Pronab
, p. 2859 - 2865 (2007/10/02)
Addition of C6H5SCl to alkenes 8, 10, and 14 yields allyl thioethers 9, 11, and 15 + 16 after thermolysis at 120 - 200 deg C.Vinyl thioethers are not observed.The influence of substituents R1 and R2 on the regioselectivity (Table 1) and the rate of the elimination (Table 2) is examined.
