The Free Radical Addition of Thiolacetic Acid to Some Cyclic Olefins

Bordwell, F. G.; Hewett, William A.

doi:10.1021/ja01570a051

Cited by 52 publications

(16 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[15] In the case of BuSH addition to 1, rearranged 2 (R = Bu) was obtained in 52 % yield, while the addition of H 2 S to 1 in the presence of stoichiometric amounts of AlBr 3 resulted in rearrangement and dimerisation to diisobornyl sulfide. [16] Isobornyl structures have also been obtained in addition reactions of camphene and sulfides in the presence of stoichiometric amounts of triflic acid. [17] To the best of our knowledge, electrophilic functionalisation of camphene without isomerisation of the bicyclo[2.2.1]heptane structure has not been reported.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Indium Triflate‐Catalysed Addition of Thio Compounds to Camphene: A Novel Route to 2,3,3‐Trimethyl‐2‐thiobicyclo[2.2.1]heptane Derivatives

et al. 2007

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 99%

“…The radical-type addition of thioacetic acid to 1, affording the expected anti-Markovnikov compounds 3 (Scheme 1), has also been reported. [16] The use of AcSH under UV irradiation conditions thus afforded the corresponding thioacyl derivative 3 in 64 % yield with no stereochemical assignment.…”

Section: Introductionmentioning

confidence: 99%

Indium Triflate‐Catalysed Addition of Thio Compounds to Camphene: A Novel Route to 2,3,3‐Trimethyl‐2‐thiobicyclo[2.2.1]heptane Derivatives

et al. 2007

View full text Add to dashboard Cite

show abstract

“…Homolytic addition of thioacetic acid to bicyclic monoterpenes such as b-pinene or camphene has been extensively studied [8,9]. In both cases, it results in the exclusive formation of thioacetates on the less hindered part of the exo methylene bond as expected by the Kharash rule.…”

Section: Discussionmentioning

confidence: 99%

An unusual rearrangement of the thujane skeleton under free-radical conditions: Synthesis of thioacetates and thiols derivatives of (-)-sabinene

Candela

Fellous

Joulain³

et al. 2002

Sulfur Letters

View full text Add to dashboard Cite

Photochemical acetylthiolation of (À)-sabinene 1 afforded 10-acetylthiothujane 2 and an unexpected cyclopentenyl methyl thioacetate 3 in moderate yield (24%). Hydride reduction of these two latter compounds gave two monoterpenoid thiols (2a and 3a) in excellent yield (95%). The odour of the major sulfur-containing compounds 2 and 2a was respectively described as being typically anisic and as reminiscent of cooked leek. Structural determination of these derivatives was achieved by one-and two-dimensional NMR spectroscopy.

show abstract

“…Reactions of α‐ and β‐pinene with different sulfur‐containing compounds have been described that lead to a variety of products. For instance, Bordwell and Hewitt reported that, under the influence of UV irradiation, α‐ and β‐pinene reacted with thioacetic acid to produce 3‐pinanyl and 10‐pinanyl thioacetate, respectively, whilst no p ‐menthene compounds were observed in the respective products . The addition of mercaptoacetic acid to several types of terpene, that is, limonenes, α‐ and β‐pinene, camphene, and myrcene, was reported by Buess et al .…”

Section: Thiol–ene Reactions For the Synthesis Of Diverse Valuable Plmentioning

confidence: 93%

Thiol–Ene (Click) Reactions as Efficient Tools for Terpene Modification

Firdaus

2017

Asian J Org Chem

View full text Add to dashboard Cite

This Focus Review highlights the application of thiol-ene (click) chemistry to the productiono fadiverse range of materials that are derived from terpenes. To present an overview concerning the potencyo ft erpenes as renewable resources, recent advances in their developmentb y using synthetic organic chemistry are initially discussed. In addition, the use of thiol-enec hemistry as an efficient approach and versatile tool for noncatalytic carbonÀheteroatom bond formation is briefly presented, including mecha-nistic and kinetic aspects, as well as some structuralc onsiderations,t hat is, the influenceo ft he thiol and olefin structures, which should be well-thought-out before applying such chemistry.T his discussiona lso coversh ow an initiator works and its effect on the reactionr ate. Moreover,t he utilization of thiol-ene reactions for the synthesis of terpenebased valuable platform chemicals, monomers, and polymers, includingr ecent examples that demonstrate its broad utility,a re highlighted.[a] Dr.M.F irdaus Scheme11. Terpene-basedp olythioethers thatwere prepared by thiol-ene photopolymerization. [100] Scheme12. Preparation of cross-linkedthin films that were derived from limonene and their possible addition type. [101] Asian

show abstract

The Free Radical Addition of Thiolacetic Acid to Some Cyclic Olefins

Cited by 52 publications

References 0 publications

Indium Triflate‐Catalysed Addition of Thio Compounds to Camphene: A Novel Route to 2,3,3‐Trimethyl‐2‐thiobicyclo[2.2.1]heptane Derivatives

Indium Triflate‐Catalysed Addition of Thio Compounds to Camphene: A Novel Route to 2,3,3‐Trimethyl‐2‐thiobicyclo[2.2.1]heptane Derivatives

An unusual rearrangement of the thujane skeleton under free-radical conditions: Synthesis of thioacetates and thiols derivatives of (-)-sabinene

Thiol–Ene (Click) Reactions as Efficient Tools for Terpene Modification

Contact Info

Product

Resources

About