I. W. J. STILL
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View article: α-Oxosulfines: reactions with alkenes and alkynes
α-Oxosulfines: reactions with alkenes and alkynes Open
Thiochroman-4-one 1,1-dioxide has been successfully converted into 3-sulfinylthiochroman-4-one 1,1-dioxide and the reactions of this α-oxosulfine with a series of alkenes have been carefully investigated. The α-oxosulfine was found to reac…
View article: Approaches to the tetracyclic eudistomins: the synthesis of N(10)-acetyleudistomin L
Approaches to the tetracyclic eudistomins: the synthesis of N(10)-acetyleudistomin L Open
The successful synthesis of the tetracyclic ring system present in eudistomins C, E, K, and L involves a convergent approach to N(10)-acetyleudistomin L from 5-bromo-N′-hydroxytryptamine and a suitably protected cysteinal derivative. Ring …
View article: The synthesis and reactivity of α-oxosulfines
The synthesis and reactivity of α-oxosulfines Open
Thiochroman-4-one and cyclohexanone have been converted into the corresponding α-oxosulfines and the behaviour of these reactive intermediates with a range of alkenes and alkynes has been examined. In contrast to some earlier work, the maj…
View article: The Synthesis of Eudistomins S and T: b-carbolines from the Tunicate Eudistoma olivaceum
The Synthesis of Eudistomins S and T: b-carbolines from the Tunicate Eudistoma olivaceum Open
libJtract -The syntheses of two k-arbnlines, eodistomins S and T, have been accomplished from tryptarnine precursors.Since the first reported activity against Her~es sim~lex virus, type I (HSV-l), by t,he tunicate (ancidian) organism Eudis…
View article: A general route to the synthesis of 3-alkylidene derivatives of 4-thiochromanone 1,1-dioxide
A general route to the synthesis of 3-alkylidene derivatives of 4-thiochromanone 1,1-dioxide Open
The reactions of the trimethylsilyl enol ethers of both 4-thiochromanone and 4-thiochromanone 1,1-dioxide with various carbonyl compounds complexed with titanium tetrachloride give moderate yields of the previously unknown 3-alkylidene con…
View article: Chemical behavior of an α-azidosulfide, and the related sulfoxide and sulfone, in the tetrahydrothiophene series
Chemical behavior of an α-azidosulfide, and the related sulfoxide and sulfone, in the tetrahydrothiophene series Open
The thermal, photochemical, base-catalyzed, and Lewis acid-catalyzed reactivity of 2-azidotetrahydrothiophene (1a) and the related α-azidosulfoxide and sulfone have been found to lead to a number of interesting rearrangement products. The …
View article: Conformational analysis and photochemical behavior of sulfoxides in the naphtho[1,2-<i>b</i>]thiopyran and naphtho[2,1-<i>b</i>]thiopyran series
Conformational analysis and photochemical behavior of sulfoxides in the naphtho[1,2-<i>b</i>]thiopyran and naphtho[2,1-<i>b</i>]thiopyran series Open
The sulfoxides derived from 2,3-dihydro-4H-naphtho[1,2-b]thiopyran and its 4-phenyl and 4-oxo derivatives, as well as the analogous sulfoxides in the 2,3-dihydro-1H-naphtho[2,1-b]thiopyran series, have been synthesized and their structures…
View article: Phosphorus Pentasulfide and Thiophosphoryl Bromide: Facile Reagents for the Reduction of Sulfines to Thiones
Phosphorus Pentasulfide and Thiophosphoryl Bromide: Facile Reagents for the Reduction of Sulfines to Thiones Open
View article: The reaction of malondiamides with disulfur dichloride: a reinvestigation
The reaction of malondiamides with disulfur dichloride: a reinvestigation Open
The reactions of a series of N,N′-dialkyl and N,N′-diaryl malondiamides with disulfur dichloride have been reinvestigated. The claim, made almost 60 years ago. that the products of this reaction are dithioketones R 2 CS 2 , is shown to be …
View article: Photochemical rearrangements of 2-azido-4-thiochromanone 1-oxide and 1,1-dioxide: formation of 2<i>H</i>-benzo[f]-1,2-thiazepine derivatives
Photochemical rearrangements of 2-azido-4-thiochromanone 1-oxide and 1,1-dioxide: formation of 2<i>H</i>-benzo[f]-1,2-thiazepine derivatives Open
Photolysis of 2-azido-4-thiochromanone 1,1-dioxide in benzene or dichloromethane leads to the formation of 2H-benzo[f]-1,2-thiazepin-5-one 1,1-dioxide, in very good yield. In contrast, the photolysis of the analogous sulfoxide was much mor…
View article: Correlation of the photoelectron and electronic spectra of thiochromones and thiochromanones with their electrochemical data
Correlation of the photoelectron and electronic spectra of thiochromones and thiochromanones with their electrochemical data Open
The gas phase ionization potentials, electrochemical redox potentials and spectroscopic properties of a series of thiochroman-4-one and thiochromone derivatives have been studied. A dramatic shift in the energies of the lowest vacant and h…
View article: Photochemical rearrangements of substituted thiochromanone sulfoxides
Photochemical rearrangements of substituted thiochromanone sulfoxides Open
The photochemical behavior of a number of substituted derivatives of thiochroman-4-one 1-oxide has been examined. In contrast to the analogous sulfones these sulfoxides undergo a variety of photochemical rearrangements. At least three dist…
View article: Carbon-13 nuclear magnetic resonance spectra of organic sulfur compounds. Comparison of chemical shifts for carbonyl and thiocarbonyl compounds in the pyrone, thiopyrone, and pyridone series
Carbon-13 nuclear magnetic resonance spectra of organic sulfur compounds. Comparison of chemical shifts for carbonyl and thiocarbonyl compounds in the pyrone, thiopyrone, and pyridone series Open
13 C nmr data have been obtained for a series of 2- and 4-pyrones and pyridones, and their sulfur-containing analogues. Correlations have been observed between the nature of the ring hetero-atom and the chemical shift difference (Δδ) for t…
View article: 6,8,8-Trimethyl-6-(<i>o</i>-methylthiobenzoyl)-4-thia-benzocyclooctenone. A Novel Product from the Attempted Base-catalyzed Methylation of 3-Methylthiochroman-4-one
6,8,8-Trimethyl-6-(<i>o</i>-methylthiobenzoyl)-4-thia-benzocyclooctenone. A Novel Product from the Attempted Base-catalyzed Methylation of 3-Methylthiochroman-4-one Open
The structure of the unusual eight-membered cyclic ketone 3 obtained on treatment of 3-methylthiochroman-4-one with methyl iodide in the presence of potassium t-butoxide has been assigned on the basis of n.m.r. ( 13 C and 1 H), i.r., and m…
View article: The Structures of the Trihydroxyflavans from the Acid-catalyzed Rearrangement and Dimerization of 3-Carene-2,5-dione
The Structures of the Trihydroxyflavans from the Acid-catalyzed Rearrangement and Dimerization of 3-Carene-2,5-dione Open
The structures of the trimethyl ethers of three of the four mechanistically probable trihydroxyflavans derived by acid-catalyzed rearrangement and dimerization of 3-carene-2,5-dione have been assigned on spectroscopic grounds and by analog…
View article: Acetone-sensitized photodimenzation of 3-carene-2,5-dione
Acetone-sensitized photodimenzation of 3-carene-2,5-dione Open
Ultraviolet irradiation of 3-carene-2,5-dione 1 in acetone has been found to yield three cyclobutanetype photodimers. A detailed spectroscopic study of these compounds has shown that the two most abundant dimers possess the head-to-head or…
View article: Studies in the cycloheptane field
Studies in the cycloheptane field Open
In Section I, some of the reactions of tropilidene (or cycloheptatriene) are described. Attempts to convert tropilidene directly into tropone, or the so far unknown tropyl alcohol, by employing a variety of common oxidative procedures, hav…