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Record W1903117926 · doi:10.1002/047084289x.rg010

Glyoxylic Acid Diethyl Dithioacetal

2001· reference-entry· en· W1903117926 on OpenAlexaff
Gordon S. Bates

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2001
Typereference-entry
Languageen
FieldChemistry
TopicCrystal structures of chemical compounds
Canadian institutionsUniversity of British Columbia
Fundersnot available
KeywordsGlyoxylic acidChemistryComputer scienceOrganic chemistry

Abstract

fetched live from OpenAlex

(1; R1 = Et, R2 = H) [10490-06-9] C6H12O2S2 (MW 180.32) InChI = 1S/C6H12O2S2/c1-3-9-6(5(7)8)10-4-2/h6H,3-4H2,1-2H3,(H,7,8) InChIKey = XMLOHHSISONECN-UHFFFAOYSA-N (2; R1 = (CH2)2, R2 = H) [5616-65-9] C4H6O2S2 (MW 150.24) InChI = 1S/C4H6O2S2/c5-3(6)4-7-1-2-8-4/h4H,1-2H2,(H,5,6) InChIKey = DSOVOUOPKYLGID-UHFFFAOYSA-N (3; R1 = (CH2)3, R2 = H) [20461-89-6] C5H8O2S2 (MW 164.27) InChI = 1S/C5H8O2S2/c6-4(7)5-8-2-1-3-9-5/h5H,1-3H2,(H,6,7) InChIKey = BZBYEAWKJNCPLB-UHFFFAOYSA-N (4; R1 = Et, R2 = Me [38564-39-5] C7H14O2S2 (MW 194.35) InChI = 1S/C7H14O2S2/c1-4-10-7(11-5-2)6(8)9-3/h7H,4-5H2,1-3H3 InChIKey = BTADPPRQZFQLLV-UHFFFAOYSA-N (5; R1 = Et, R2 = Et) [20461-95-4] C8H16O2S2 (MW 208.38) InChI = 1S/C8H16O2S2/c1-4-10-7(9)8(11-5-2)12-6-3/h8H,4-6H2,1-3H3 InChIKey = DGQHHBMWVOYSHU-UHFFFAOYSA-N (6; R1 = (CH2)2, R2 = Et) [20461-99-8] C6H10O2S2 (MW 178.30) InChI = 1S/C6H10O2S2/c1-2-8-5(7)6-9-3-4-10-6/h6H,2-4H2,1H3 InChIKey = OMCSHTHLIQOHDD-UHFFFAOYSA-N (7; R1 = (CH2)3, R2 = Me) [56579-84-1] C6H10O2S2 (MW 178.30) InChI = 1S/C6H10O2S2/c1-8-5(7)6-9-3-2-4-10-6/h6H,2-4H2,1H3 InChIKey = KAXSFBNZPWBKDH-UHFFFAOYSA-N (8; R1 = (CH2)3, R2 = Et) [20462-00-4] C7H12O2S2 (MW 192.33) InChI = 1S/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3 InChIKey = ANEDZEVDORCLPM-UHFFFAOYSA-N (α-keto equivalent; alkylation of the anions, aldol condensations, and both 1,2- and 1,4-additions to α,β-unsaturated compounds; thioketene and α-oxo dithioester precursor) Alternate Names: (1) bis(ethylthio)acetic acid; (2) 1,3-dithiolane-2-carboxylic acid; (3) 1,3-dithiane-2-carboxylic acid. Physical Data: (1) bp 110 °C/0.2 mmHg. (2) mp 90–91 °C. (3) mp 114.5–116 °C. (4) bp 125–127 °C/5 mmHg. (5) bp 70 °C/0.1 mmHg. (8) bp 105 °C/0.6 mmHg. (7) bp 102 °C/2 mmHg. (8) bp 75–77 °C/0.2 mmHg. Preparative Methods: esters (5), (6), and (8) are available from commercial sources. The thioacetal acids may be prepared by thioacetalization of glyoxylic acid monohydrate3 or by reaction on the appropriate thiol(ate) with 2,2-dichloroacetic acid (or the diethyl acetal) directly4 or under phase transfer5 conditions using Aliquat 336. The esters may be obtained via similar exchange processes or via acid-catalyzed esterification of the corresponding acids.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: none
GenreCandidate signal: Dataset · Consensus signal: none
Teacher disagreement score0.043
Threshold uncertainty score0.142

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0020.001
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0010.001
Science and technology studies0.0010.000
Scholarly communication0.0000.001
Open science0.0010.001
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0430.025

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.013
GPT teacher head0.242
Teacher spread0.229 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designNot applicable
Domainnot available
GenreDataset

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

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Citations0
Published2001
Admission routes1
Has abstractyes

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