MétaCan
Menu
Back to cohort
Record W2291280188 · doi:10.14288/1.0062183

The synthesis of anti-8-tricyclo [3.2.1.0 2,4] octanol and solvolysis of its p-bromobenzenes-ulphonyl derivative

2011· article· en· W2291280188 on OpenAlexaff
June I. Wells

Bibliographic record

VenuecIRcle (University of British Columbia) · 2011
Typearticle
Languageen
FieldChemistry
TopicOrganic Chemistry Cycloaddition Reactions
Canadian institutionsUniversity of British Columbia
Fundersnot available
KeywordsSolvolysisDerivative (finance)ChemistryMedicinal chemistryStereochemistryOrganic chemistryHydrolysisEconomics

Abstract

fetched live from OpenAlex

The synthesis of anti-8-tricyclo [3.2.1.0[superscript 2,4]] octanol has been carried out by the cuprous chloride catalysed reaction of diazomethane on anti-7-norbornenol. X-ray crystallographic analysis of the p-bromo-benzene sulphonyl (brosylate) derivative has unambiguously shown the cyclopropyl group to be exo. Methylene addition to norbornene and 7-norbornadienyl acetate was achieved by the above method; for the latter, the two isomers whose presence was detected by n.m.r. could not be separated. The slow rate of the acetolysis of the brosylate of anti-8-tricyclo [3.2.1.0[superscript 2,4]] octanol suggests that this derivative resembles 7-norbornyl brosylate in solvolysis reactions, rather than anti-7-norbornenyl brosylate. Enthalphy of activation calculated for the tricyclic brosylate solvolysis is of the same order as that for the 7-norbornyl case. Product studies on material isolated from samples solvolysed up to the half life of the brosylate suggest the first product probably is anti-8-tricyclo [3.2.1.0[superscript 2,4] octanyl acetate. Prolonged solvolysis conditions result in a variety of products in which the cyclopropyl group has rearranged. The structures of these products could not be determined.

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 distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesInsufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: none
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.832
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.001
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0010.000

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 head0.009
GPT teacher head0.162
Teacher spread0.153 · 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 teacher head, not a consensus.

Study designBench or experimental
Domainnot available
GenreEmpirical

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".

Quick stats

Citations0
Published2011
Admission routes1
Has abstractyes

Explore more

Same venuecIRcle (University of British Columbia)Same topicOrganic Chemistry Cycloaddition ReactionsFrench-language works237,207