220176-07-8

Upstream product

• 505-23-7 1,3 dithiane 
• 123-11-5 4-methoxy-benzaldehyde 
• 13411-42-2 2-(trimethylsilyl)-1,3-dithiane 
• 36049-90-8 2-lithio-1,3-dithiane 

Downstream Products

• 840522-75-0 2-[(4-methoxy-phenyl)-prop-2-ynyloxy-methyl]-[1,3]dithiane 
• 1450842-96-2 C₁₉H₂₂O₂S₂ 
• 6316-54-7 4-methoxy-benzoic acid benzyl ester 
• 1440963-41-6 2-(benzyloxy)-2-(4-methoxyphenyl)acetaldehyde 
• 644980-96-1 2-(4-methoxyphenyl)-6,7-dihydro-5H-1,4-dithiepine 

Relevant academic research and scientific papers

Aniline mediated oxidative C-C bond cleavage of α-alkoxy aldehydes in air and a model reaction for the synthesis of α-(d)-amino acid derivatives

A metal-free and 4-methyl aniline mediated method for the oxidative C-C bond cleavage has been developed. The reaction proceeds in air using molecular oxygen as the oxidant, affording one-carbon shortened esters in moderate to good yields within a short time. Moreover, it provides a model reaction for the highly enantioselective synthesis of (d)-serine esters by combining with a l-proline catalyzed Mannich reaction.

P(i-PrNCH2CH2)3N: an efficient catalyst for TMS-1,3-dithiane addition to aldehydes

Herein we report the use of commercially available P(i-PrNCH2CH2)3N (1a) as an efficient catalyst for 2-trimethylsilyl-1,3-dithiane (TMS-dithiane) addition to aldehydes at room temperature. The catalyst loading required fo

Lewis base catalyzed 1,3-dithiane addition to carbonyl compounds using 2-trimethylsilyl-1,3-dithiane

1,3-Dithiane addition to various aldehydes and ketones using 2-trimethylsilyl-1,3-dithiane in the presence of a catalytic amount of a Lewis base such as tetrabutylammonium phenoxide (PhONn-Bu4) proceeds smoothly to afford the corresponding α-hy

Mercury(II) chloride-mediated cyclization - Rearrangement of O-propargylglycolaldehyde dithioacetals to 3-pyranone dithioketals: An expeditious access to 3-pyranones

(Chemical Equation Presented) O-Propargyl glycolaldehyde dithioacetals undergo a unique cyclization-rearrangement in the presence of mercuric chloride and calcium carbonate to afford 3-pyranones exclusively or along with 2,5-dihydrofuran-3-carboxaldehydes

Electronic control of product formation in the rearrangement of 1,3-dithian-2-yl-arylmethanols

1,3-Dithian-2-yl-phenylmethanols undergo efficient rearrangement to afford 2-phenyl-6,7-dihydro-5H-1,4-dithiepines. The reactions were found to show remarkable variation in products formation that is dictated by the substituents on the aryl ring.

New, practical and effective sources of fluoride ion for desilylation to form carbon anions

Suspensions of powdered glassy solids prepared by fusion of 1:1 mixtures of CsF-CsOH and CsF-CsCl effectively catalyze the generation of enolates, acetylide and other anions from trimethylsilylated precursors.

An efficient photo-SET-induced cleavage of dithiane-carbonyl adducts and its relevance to the development of photoremovable protecting groups for ketones and aldehydes

Irradiation of dithiane-aldehyde/ketone adducts in the presence of benzophenone leads to C-C bond cleavage regenerating the carbonyl compounds. It is established that the mechanism of this reaction involves photochemically induced single electron transfer from the dithiane moiety to the excited molecule of ET-photosensitizer, accompanied by mesolytic C-C cleavage in the generated cation-radical, which is assisted by the anion- radical of benzophenone. This mechanism is confirmed by a Hammett plot study of the cleavage in the dithiane adducts of substituted aromatic aldehydes and a deuterium kinetic isotope effect study. Ab initio computations at UHF/6- 31G* and MP2/6-31G* levels of theory in conjunction with self-consistent reaction field (self-consistent isodensity-polarized continuum model), to account for the solvent effect, also support the experimental findings. The reaction is most efficient for protection of aromatic aldehydes and ketones and aliphatic ketones, and is a novel method for protecting carbonyl functionalities with a photoremovable group.