75697-56-2Relevant academic research and scientific papers
1-PHENYLTHIO-1-(TRIMETHYLSILOXY)CYCLOPROPANES VIA THE SILA-PUMMERER REARRANGEMENT
Bhupathy, M.,Cohen, Theodore
, p. 4793 - 4796 (2007/10/02)
This first study of the sila-Pummerer rearrangement in a cyclopropane system reveals that several 1-trimethylsiloxy-1-(phenylthio)cyclopropanes can be prepared stereoselectively through putative sulfur-stabilized carbocationic intermediates.
1-METHOXY-1-(PHENYLTHIO)CYCLOPROPANES FROM OLEFINS VIA THE PUMMERER REARRANGEMENT
Bhupathy, M.,Cohen, Theodore
, p. 4797 - 4800 (2007/10/02)
The Pummerer rearrangements of cyclopropyl(methoxy)phenylsulfonium salts proceed via sulfur-stabilized carbocations to yield the title compounds.The sulfonium salts were prepared in high yields from olefins via carbene addition, oxidation, and methylation
PRACTICAL METHOD FOR USING ALKOXIDE-ACCELERATED VINYLCYCLOBUTANE RING EXPANSIONS IN THE SYNTHESIS OF SIX-MEMBERED RINGS. UNEXPECTED ORBITAL SYMMETRY ALLOWED AND FORBIDDEN 1,3-SIGMATROPIC REARRANGEMENTS.
Cohen,Bhupathy,Matz
, p. 520 - 525 (2007/10/02)
A practical method for utilizing the ring expansion of 2-vinylcyclobutanols to cyclohex-3-en-1-ols, even in cases in which very acid-sensitive groups are present, consists of the addition of 1-lithio- 1-methoxycyclopropanes to conjucated enals, brief trea
The chemistry of small ring compounds. Part 46. Reduction of 1-halocyclopropyl sulfides by thiolates
Jorritsma, R.,Steinberg, H.,Boer, Th. J. de
, p. 288 - 298 (2007/10/02)
The reaction of 1-halocyclopropyl sulfides with sodium alkanethiolates in protic or aprotic solvents leads to high yields of cyclopropyl sulfides, in which halogen has been replaced by hydrogen.The complementary oxidized product is, in most cases, the thioketone or thioaldehyde derived from the alkanethiolate.The reduction is unaffected by radical scavengers or by one-electron donors.Reaction kinetics indicate that the reduction proceeds via the 1-(alkylthio)cyclopropyl cation.A mechanism is discussed (Scheme 9) in which this ambident cation is attacked by thiolate on sulfur.In the intermediary sulfonium ylid an intramolecular hydrogen shift leads to the observed products.
The chemistry of small ring compounds. Part 44. Solvolysis of cyclopropyl sulfides and ethers
Jorritsma, R.,Steinberg, H.,Boer, Th. J. de
, p. 194 - 200 (2007/10/02)
1-Chlorocyclopropyl methyl ether and the corresponding sulfide are methanolysed without any rupture of the three-membered ring.The solvolysis of 1-halocyclopropyl sulfides has been studied kinetically and takes place via an SN1 mechanism.Methyl
A SYNTHESIS OF 2-VINYLCYCLOBUTANONES USING 1-METHOXYCYCLOPROYLLITHIUM REAGENTS
Cohen, Theodore,Matz, James R.
, p. 2455 - 2458 (2007/10/02)
A facile synthesis of 2-vinylcyclobutanones consists of reductive lithiation of 1-phenylthio-1-methoxycyclopropanes, addition of enals or enones to the resulting α-lithioethers, and acid catalyzed rearrangement of the allylic alcohols thus produced.
